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Scores for 2012-2011
| Date | Sport | Opponent | Venue | Result | |
| May 26 | Varsity Crew (Boys) | NEIRA | LK Quinsigamond | ||
| May 26 | Varsity Crew (Girls) | NEIRA | LK Quinsigamond | ||
| May 23 | Junior Varsity Crew (Boys) | Lower Boat Championship | Lake Waramaug | ||
| May 23 | Varsity Golf (Coed) | Kingswood Tournament | Oakridge Golf Club | ||
| May 19 | Junior Varsity Lacrosse (Boys) | Exeter | Away | Win, 12-6 | |
| May 19 | Varsity Lacrosse (Boys) | Exeter | Away | Win, 6-5 (2 OT) | |
| May 19 | Varsity Cycling (Coed) | New England's | Proctor | Win, 1st | |
| May 19 | Junior Varsity Baseball (Boys) | Choate | Away | Loss, 10-8 | |
| May 19 | Varsity Crew (Girls) | Gunnery/MPS/Choate | Gunnery | ||
| May 19 | Junior Varsity Golf (Coed) | Loomis | CC of Greenfield | Loss, LC 259, DA 263 | |
| May 19 | Varsity Golf (Coed) | NMH | Away | Win, DA 334, NMH 336 | |
| May 19 | Varsity Crew (Boys) | Gunnery and Choate | Away | ||
| May 19 | Junior Varsity Crew (Boys) | Gunnery and Choate | Gunnery | ||
| May 19 | Junior Varsity Tennis (Girls) | Andover | Home | Loss, 5-2 | |
| May 19 | Junior Varsity Lacrosse (Girls) | Exeter | Away | Loss, 10-6 | |
| May 19 | Varsity Lacrosse (Girls) | Exeter | Away | Win, 21-14 | |
| May 19 | Varsity Water Polo (Girls) | New England's | Exeter | 2nd Place | |
| May 19 | Varsity Baseball (Boys) | Walker Tournament | Choate | 1st place - 10-4 (Choate), 5-0 (NMH) | |
| May 19 | Varsity Track (Coed) | New England's | Choate | Boys 1st, Girls 8th | |
| May 19 | Varsity Tennis (Boys) | New England's | Choate | Loss, 4-3 (Choate) | |
| May 19 | Varsity Tennis (Girls) | Kent Tournament | Away | ||
| May 18 | Reserve Lacrosse (Boys) | Monson | CANCELLED | ||
| May 17 | Varsity Softball (Girls) | Stoneleigh | Away | Win, 8-4 | |
| May 16 | Varsity Water Polo (Girls) | Hopkins | Deerfield Academy | Win, 9-3 | |
| May 16 | Varsity Lacrosse (Boys) | Salisbury | Home | Win, 11-10 (OT) | |
| May 16 | Junior Varsity Lacrosse (Boys) | Salisbury | Home | Win, 9-3 | |
| May 16 | Varsity Tennis (Boys) | Cheshire | Away | Win, 4-1 | |
| May 16 | Reserve Lacrosse (Boys) | Loomis | CANCELLED | ||
| May 16 | Reserve Lacrosse (Girls) | Charlemont | Home | Win, 12-5 | |
| May 16 | Varsity Baseball (Boys) | Avon | Home | Loss, 9-3 | |
| May 16 | Junior Varsity Baseball (Boys) | Cushing | Away | Loss, 9-0 | |
| May 16 | Junior Varsity Lacrosse (Girls) | Williston | Away | Loss, 14-13 | |
| May 16 | Junior Varsity Tennis (Boys) | Eaglebrook | Home | Win, 4-3 | |
| May 16 | Varsity Softball (Girls) | Loomis | Away | Loss, 5-4 | |
| May 16 | Varsity Lacrosse (Girls) | Berkshire | Home | Loss, 17-16 (OT) | |
| May 16 | Junior Varsity Golf (Coed) | Cushing | Away | ||
| May 16 | Varsity Golf (Coed) | Westmiinster and Williston | Away | Loss | |
| May 16 | Varsity Cycling (Coed) | Profile Road Race | Away | ||
| May 14 | Varsity Lacrosse (Girls) | Cushing | Away | Win, 16-7 | |
| May 14 | Varsity Tennis (Boys) | Suffield | CANCELLED | ||
| May 14 | Reserve Lacrosse (Boys) | Loomis | CANCELLED | ||
| May 14 | Varsity Baseball (Boys) | Williston | Away | rainout in 4th innning (4-1 DA) | |
| May 14 | Junior Varsity Baseball (Boys) | NMH | Away | Loss, 10-8 | |
| May 14 | Varsity Softball (Girls) | Stoneleigh | CANCELLED | ||
| May 14 | Reserve Lacrosse (Girls) | Bement | Home | Win, 12-8 | |
| May 14 | Junior Varsity Tennis (Boys) | Eagle Hill | CANCELLED | ||
| May 14 | Varsity Golf (Coed) | New England's Girl's | Taft | ||
| May 12 | Varsity Lacrosse (Boys) | Avon | Away | Win, 13-6 | |
| May 12 | Reserve Lacrosse (Boys) | Avon | CANCELLED | ||
| May 12 | Varsity Cycling (Coed) | Exeter | Away | W | |
| May 12 | Junior Varsity Golf (Coed) | Eagle Hill and Bement | Away | ||
| May 12 | Reserve Lacrosse (Girls) | Taft | Away | Win, 15-4 | |
| May 12 | Varsity Crew (Boys) | Middlesex and Nobles | Home | ||
| May 12 | Varsity Softball (Girls) | Andover | Away | Loss, 15-0 | |
| May 12 | Varsity Golf (Coed) | Hotchkiss Quint | Away | ||
| May 12 | Varsity Water Polo (Girls) | Andover & Hopkins | Andover | PA 7-DA 6; DA 10, HOP 5 | |
| May 12 | Varsity Tennis (Boys) | Exeter | Away | Loss, 4-2 | |
| May 12 | Junior Varsity Lacrosse (Boys) | Avon | Away | Win, 7-5 | |
| May 12 | Varsity Track (Coed) | NMH and Exeter | NMH | Boys 1st, Girls 2nd | |
| May 12 | Varsity Crew (Girls) | Middlesex and Nobles | Away | ||
| May 12 | Junior Varsity Tennis (Boys) | Exeter | Away | Loss, 6-1 | |
| May 12 | Junior Varsity Tennis (Girls) | Choate | Away | Win, 5-2 | |
| May 12 | Varsity Tennis (Girls) | Choate | Away | Win, 6-1 | |
| May 12 | Junior Varsity Crew (Boys) | Rumsey Hall | Home | ||
| May 12 | Varsity Baseball (Boys) | Andover | Away | Loss, 2-0, 6-0 (DH) | |
| May 12 | Junior Varsity Baseball (Boys) | Andover | Away | Win, 8-5 | |
| May 9 | Varsity Lacrosse (Boys) | Kent | Away | Win, 15-4 | |
| May 9 | Varsity Tennis (Boys) | Hotchkiss | Home | Loss, 7-0 | |
| May 9 | Varsity Lacrosse (Girls) | KUA | Home | Win, 15-4 | |
| May 9 | Junior Varsity Baseball (Boys) | Cardigan | CANCELLED | ||
| May 9 | Varsity Tennis (Girls) | Longmeadow | CANCELLED | ||
| May 9 | Junior Varsity Tennis (Girls) | Worcester | CANCELLED | ||
| May 9 | Varsity Cycling (Coed) | White Mountain | Away | 5th | |
| May 9 | Varsity Softball (Girls) | Suffield | Away | Loss, 8-0 | |
| May 9 | Varsity Golf (Coed) | Choate | Away | Win, 203-227 | |
| May 9 | Reserve Lacrosse (Girls) | Cushing | CANCELLED | ||
| May 9 | Varsity Water Polo (Girls) | Suffield | Home | Win, 14-7 | |
| May 9 | Junior Varsity Tennis (Boys) | Loomis | CANCELLED | ||
| May 9 | Junior Varsity Lacrosse (Boys) | Eaglebrook | Home | Win, 7-3 | |
| May 9 | Reserve Lacrosse (Boys) | Eaglebrook | CANCELLED | ||
| May 9 | Junior Varsity Golf (Coed) | Kingswood and NMH | Home | Win, 245 (DA), 254 (NMH), 261 (K-O) | |
| May 9 | Varsity Baseball (Boys) | NMH | Away | Win, 8-2 | |
| May 7 | Varsity Tennis (Girls) | NMH | Home | Win, 8-1 | |
| May 7 | Varsity Lacrosse (Girls) | Williston | Away | Loss, 13-8 | |
| May 6 | Varsity Crew (Girls) | Weyland/Weston | Away | ||
| May 6 | Varsity Crew (Boys) | Weyland/Weston | Away | ||
| May 6 | Junior Varsity Crew (Boys) | Weyland/Weston | Away | ||
| May 5 | Junior Varsity Lacrosse (Girls) | Hotchkiss | Home | Win, 11-6 | |
| May 5 | Junior Varsity Lacrosse (Boys) | Hotchkiss | Home | Win, 9-8 (OT) | |
| May 5 | Varsity Lacrosse (Girls) | Hotchkiss | Home | Loss, 10-9 | |
| May 5 | Varsity Lacrosse (Boys) | Hotchkiss | Home | Win, 15-8 | |
| May 5 | Varsity Softball (Girls) | Hotchkiss | Home | Win, 10-2 | |
| May 5 | Junior Varsity Tennis (Boys) | Choate | Home | Win, 5-1 | |
| May 5 | Varsity Track (Coed) | Choate | Home | Boys: W, Girls: L | |
| May 5 | Varsity Golf (Coed) | Andover | Home | Win | |
| May 5 | Varsity Baseball (Boys) | Worcester | Home | Loss, 8-5 | |
| May 5 | Varsity Tennis (Boys) | Choate | Home | Win, 4-3 | |
| May 5 | Junior Varsity Tennis (Girls) | Loomis | Home | Win, 7-0 | |
| May 5 | Varsity Tennis (Girls) | Loomis | Home | Win, 6-1 | |
| May 5 | Varsity Water Polo (Girls) | Williston | Home | Win, 14-8 | |
| May 5 | Junior Varsity Baseball (Boys) | Eaglebrook | Home | Loss, 6-3 | |
| May 5 | Reserve Lacrosse (Girls) | Loomis | Home | Win, 16-3 | |
| May 5 | Reserve Lacrosse (Boys) | Cushing | CANCELLED | ||
| May 4 | Reserve Lacrosse (Boys) | Loomis | Home | ||
| May 2 | Varsity Lacrosse (Boys) | Lawrenceville | Choate | Loss, 7-6 | |
| May 2 | Junior Varsity Lacrosse (Boys) | Cardigan | Away | Win, 12-8 | |
| May 2 | Varsity Cycling (Coed) | Killington | CANCELLED | ||
| May 2 | Reserve Lacrosse (Boys) | Loomis | CANCELLED | ||
| May 2 | Junior Varsity Lacrosse (Girls) | Loomis | Away | Win, 7-6 | |
| May 2 | Junior Varsity Crew (Girls) | NMH | Home | ||
| May 2 | Junior Varsity Crew (Boys) | NMH | Away | ||
| May 2 | Varsity Lacrosse (Girls) | Loomis | Away | Loss, 19-6 | |
| May 2 | Junior Varsity Tennis (Boys) | Westminster | Away | Win, 6-1 | |
| May 2 | Varsity Water Polo (Girls) | Loomis | Away | Loss, 11-8 | |
| May 2 | Junior Varsity Golf (Coed) | Williston | Home | Win, 6-0 | |
| May 2 | Varsity Tennis (Boys) | Westminster | Away | Win, 7-0 | |
| May 2 | Varsity Baseball (Boys) | Cushing | Away | Loss, 11-0 | |
| May 2 | Varsity Golf (Coed) | NMH | Home | Win, 7 1/2 - 1 1/2 | |
| May 2 | Junior Varsity Baseball (Boys) | NMH | Home | Loss, 6-2 | |
| May 2 | Junior Varsity Tennis (Girls) | NMH | Home | Win, 6-1 | |
| Date | Sport | Opponent | Venue | Result | |
| Apr 30 | Reserve Lacrosse (Boys) | NMH | Away | Win, 10-3 | |
| Apr 30 | Varsity Softball (Girls) | NMH | Away | Loss, 18-4 | |
| Apr 30 | Varsity Lacrosse (Boys) | NMH | Away | Win, 13-6 | |
| Apr 28 | Junior Varsity Tennis (Girls) | Hotchkiss | Home | Win, 4-3 | |
| Apr 28 | Varsity Tennis (Girls) | Hotchkiss | Home | Loss, 6-1 | |
| Apr 28 | Varsity Lacrosse (Girls) | Westminster | Home | Win, 11-6 | |
| Apr 28 | Reserve Lacrosse (Boys) | Taft | CANCELLED | ||
| Apr 28 | Varsity Track (Coed) | Loomis and Hotchkiss | Loomis | Boys: 1st Girls: 3rd | |
| Apr 28 | Junior Varsity Lacrosse (Girls) | Westminster | Home | Win, 9-8 | |
| Apr 28 | Varsity Crew (Girls) | Pomfret Quad | Away | ||
| Apr 28 | Junior Varsity Crew (Boys) | Pomf/Dextr/Sfld | Pomfret | ||
| Apr 28 | Junior Varsity Lacrosse (Boys) | Andover | Home | Win, 15-1 | |
| Apr 28 | Varsity Lacrosse (Boys) | Andover | Home | Win, 12-9 | |
| Apr 28 | Varsity Cycling (Coed) | Gould | Away | Loss | |
| Apr 28 | Varsity Crew (Boys) | Pomfret Quad | Away | ||
| Apr 28 | Junior Varsity Baseball (Boys) | Exeter | Away | CANCELLED | |
| Apr 28 | Reserve Lacrosse (Girls) | Suffield | Away | Loss, 9-7 | |
| Apr 28 | Junior Varsity Golf (Coed) | Eaglebrook | Home | Win, 4-2 | |
| Apr 28 | Varsity Water Polo (Girls) | Hopkins | Away | Win, 10-6 | |
| Apr 28 | Varsity Softball (Girls) | Williston | Home | Loss, 19-2 | |
| Apr 28 | Varsity Baseball (Boys) | Exeter | Away | 9-6 win, 5-0 loss | |
| Apr 28 | Junior Varsity Tennis (Boys) | Andover | Away | Loss, 5-2 | |
| Apr 28 | Varsity Tennis (Boys) | Andover | Away | Win, 4-3 | |
| Apr 28 | Varsity Golf (Coed) | Newport Invitational | Away | Win, 1st Place | |
| Apr 25 | Varsity Tennis (Girls) | Andover | Away | Loss, 8-1 | |
| Apr 25 | Varsity Water Polo (Girls) | Choate | Home | Win, 14-5 | |
| Apr 25 | Varsity Crew (Girls) | SMS/Groton/Middlesex | Away | ||
| Apr 25 | Varsity Lacrosse (Girls) | Greenwich | Wesleyan | Loss, 13-10 | |
| Apr 25 | Varsity Lacrosse (Boys) | Loomis | Away | Win, 9-3 | |
| Apr 25 | Varsity Baseball (Boys) | Choate | Home | Loss, 13-4 | |
| Apr 25 | Junior Varsity Lacrosse (Boys) | Loomis | Away | Win, 6-3 | |
| Apr 25 | Varsity Cycling (Coed) | Holderness | Away | Loss | |
| Apr 25 | Reserve Lacrosse (Girls) | Longmeadow | Away | Loss, 9-0 | |
| Apr 25 | Junior Varsity Baseball (Boys) | Eaglebrook | Away | Loss, 14-2 | |
| Apr 25 | Junior Varsity Tennis (Girls) | Stoneleigh | Away | Win, 6-1 | |
| Apr 25 | Junior Varsity Golf (Coed) | NMH | Away | Win, 4.5 - 2.5 | |
| Apr 25 | Varsity Golf (Coed) | Hotchkiss and Berkshire | Away | Win, DA 390, Berkshire 426, Hotchkiss 429 | |
| Apr 25 | Junior Varsity Lacrosse (Girls) | NMH | Home | Win, 14-7 | |
| Apr 25 | Varsity Tennis (Boys) | NMH | Home | Win, 7-0 | |
| Apr 25 | Junior Varsity Tennis (Boys) | NMH | Home | Win, 6-4 | |
| Apr 24 | Reserve Lacrosse (Boys) | Bement | Home | Win, 12-0 | |
| Apr 23 | Varsity Softball (Girls) | NMH | Away | Win, 18-3 | |
| Apr 22 | Varsity Cycling (Coed) | East Coast Cycling Conference | CANCELLED | ||
| Apr 21 | Junior Varsity Golf (Coed) | Taft and Salisbury | Home | Taft 226, DA 249, Salisbury 284 | |
| Apr 21 | Varsity Lacrosse (Girls) | Taft | Home | Loss, 17-8 | |
| Apr 21 | Varsity Crew (Boys) | St. Mark's and Brooks | Donahue Rowing Center | ||
| Apr 21 | Junior Varsity Lacrosse (Girls) | Taft | Home | Win, 11-9 | |
| Apr 21 | Junior Varsity Lacrosse (Boys) | Taft | Home | Win, 11-4 | |
| Apr 21 | Junior Varsity Crew (Boys) | Dublin | CANCELLED | ||
| Apr 21 | Junior Varsity Crew (Girls) | Dublin | CANCELLED | ||
| Apr 21 | Varsity Lacrosse (Boys) | Taft | Home | Win, 8-7 | |
| Apr 21 | Junior Varsity Baseball (Boys) | Avon | Home | Loss, 21-3 | |
| Apr 21 | Reserve Lacrosse (Girls) | Westminster | Home | Win, 9-4 | |
| Apr 21 | Varsity Tennis (Boys) | Kent | Away | Win, 7-0 | |
| Apr 21 | Varsity Softball (Girls) | Taft | Away | Loss, 17-3 | |
| Apr 21 | Varsity Water Polo (Girls) | Andover and Greenwich HS | Home | Loss, 12-11 OT; 10-8 | |
| Apr 21 | Junior Varsity Tennis (Boys) | Cardigan | Away | CANCELLED | |
| Apr 21 | Varsity Golf (Coed) | Taft | Home | Win, DA 397, Taft 425 | |
| Apr 21 | Reserve Lacrosse (Boys) | Avon | CANCELLED | ||
| Apr 21 | Varsity Tennis (Girls) | Williston | Away | Win, 7-0 | |
| Apr 21 | Varsity Track (Coed) | Hunt Relays | Home | ||
| Apr 21 | Junior Varsity Tennis (Girls) | Williston | Away | Win, 7-0 | |
| Apr 21 | Varsity Baseball (Boys) | Tabor | Home | Loss, 15-7, 6-4 | |
| Apr 21 | Varsity Cycling (Coed) | East Coast Cycling Conference | Dartmouth | ||
| Apr 20 | Varsity Tennis (Boys) | Williston | Away | Win, 4-0 | |
| Apr 18 | Junior Varsity Lacrosse (Boys) | Longmeadow | Home | Win, 6-5 | |
| Apr 18 | Varsity Baseball (Boys) | Worcester | Away | Loss, 8-6 | |
| Apr 18 | Junior Varsity Tennis (Boys) | Worcester | Away | Win, 7-0 | |
| Apr 18 | Varsity Lacrosse (Boys) | Trinity-Pawling | Loomis | Loss, 8-7 (OT) | |
| Apr 18 | Reserve Lacrosse (Girls) | Loomis | Away | Win, 9-2 | |
| Apr 18 | Varsity Tennis (Boys) | Loomis | Away | Win, 4-3 | |
| Apr 18 | Varsity Water Polo (Girls) | Exeter | Home | Loss, 21-19 | |
| Apr 18 | Junior Varsity Lacrosse (Girls) | Longmeadow | Away | Loss, 10-8 | |
| Apr 18 | Reserve Lacrosse (Boys) | Eaglebrook | CANCELLED | ||
| Apr 18 | Junior Varsity Baseball (Boys) | Cushing | Home | Loss, 15-1 | |
| Apr 18 | Varsity Lacrosse (Girls) | NMH | Home | Win, 16-5 | |
| Apr 18 | Varsity Tennis (Girls) | Suffield | Home | Win, 5-2 | |
| Apr 18 | Junior Varsity Tennis (Girls) | Suffield | Home | Win, 7-0 | |
| Apr 18 | Varsity Golf (Coed) | Wilbraham and Williston | Away | WNS 200, DA 203, WMA 218 | |
| Apr 16 | Varsity Baseball (Boys) | Springfield College | Home | Loss, 14-6 | |
| Apr 16 | Reserve Lacrosse (Girls) | Bement | Away | Win, 9-4 | |
| Apr 14 | Varsity Tennis (Girls) | Taft | Away | Win, 5-2 | |
| Apr 14 | Varsity Tennis (Boys) | Taft | Home | Win, 6-1 | |
| Apr 14 | Varsity Softball (Girls) | Choate | Home | Loss, 19-5 | |
| Apr 14 | Junior Varsity Lacrosse (Boys) | Choate | Away | Loss, 11-4 | |
| Apr 14 | Junior Varsity Lacrosse (Girls) | Choate | Away | Loss, 7-6 | |
| Apr 14 | Varsity Lacrosse (Boys) | Choate | Away | Win, 15-4 | |
| Apr 14 | Junior Varsity Tennis (Boys) | Taft | Home | Win, 5-2 | |
| Apr 14 | Junior Varsity Tennis (Girls) | Taft | Away | Loss, 4-3 | |
| Apr 14 | Varsity Track (Coed) | Andover and Taft | Home | Boys: 1st Girls: 3rd | |
| Apr 14 | Varsity Lacrosse (Girls) | Choate | Away | Loss, 13-12 | |
| Apr 14 | Varsity Water Polo (Girls) | Choate Tournament | Away | Win, 14-9 | |
| Apr 14 | Varsity Baseball (Boys) | NMH | Home | Loss, 11-9 | |
| Apr 14 | Reserve Lacrosse (Boys) | Choate | CANCELLED | ||
| Apr 14 | Varsity Golf (Coed) | Exeter | Away | Win, 81/2 - 1/2 | |
| Apr 14 | Junior Varsity Golf (Coed) | Eaglebrook | Away | Loss, 18-6 | |
| Apr 14 | Reserve Lacrosse (Girls) | Choate | CANCELLED | ||
| Apr 14 | Junior Varsity Baseball (Boys) | Williston | Away | Win, 4-2 | |
| Apr 11 | Varsity Lacrosse (Boys) | Torrey Pines | Home | Win, 11-3 | |
| Apr 11 | Varsity Softball (Girls) | Worcester | Home | Loss, 22-5 | |
| Apr 11 | Junior Varsity Lacrosse (Girls) | Andover | Home | Win, 12-6 | |
| Apr 11 | Varsity Lacrosse (Girls) | Andover | Home | Loss, 13-5 | |
| Apr 11 | Junior Varsity Baseball (Boys) | Taft | Away | Loss, 6-5 | |
| Apr 11 | Varsity Tennis (Boys) | Kingswood | Home | Win, 4-3 | |
| Apr 11 | Varsity Baseball (Boys) | Taft | Home | Loss, 8-5 | |
| Apr 11 | Junior Varsity Tennis (Boys) | Eaglebrook | Away | Loss, 8-1 | |
| Apr 11 | Junior Varsity Tennis (Girls) | Westminster | Home | Win, 6-1 | |
| Apr 11 | Varsity Golf (Coed) | Avon and NMH | Home | Win, 194, 213Avon, 208NMH | |
| Apr 11 | Varsity Water Polo (Girls) | Loomis | Home | Loss, 22-14 | |
| Apr 11 | Varsity Crew (Boys) | NMH (S) | Away | ||
| Apr 11 | Varsity Tennis (Girls) | Westminster | Home | Win, 6-1 | |
| Apr 11 | Varsity Crew (Girls) | NMH (S) | Away | ||
| Apr 11 | Junior Varsity Lacrosse (Boys) | Cardigan | Home | Win, 10-9 (OT) | |
| Apr 7 | Varsity Softball (Girls) | Miss Porter's | Away | Loss, 18-3 | |
| Apr 7 | Varsity Lacrosse (Girls) | Middlesex | Home | Loss, 11-4 | |
| Apr 7 | Junior Varsity Lacrosse (Girls) | Middlesex | Home | Loss, 12-7 | |
| Apr 7 | Junior Varsity Lacrosse (Boys) | Westminster | Away | Win, 8-5 | |
| Apr 7 | Varsity Lacrosse (Boys) | Westminster | Away | Win, 6-4 | |
| Apr 7 | Reserve Lacrosse (Girls) | Miss Porter's | Home | ||
| Apr 7 | Varsity Tennis (Girls) | Groton | Home | Win, 5-2 | |
| Apr 7 | Varsity Baseball (Boys) | Cushing | Home | Loss, 5-4 | |
| Apr 7 | Varsity Crew (Girls) | Winsor (S) | Belmont Hill | ||
| Apr 7 | Varsity Crew (Boys) | Belmont Hill (S) | Away | ||
| Apr 7 | Junior Varsity Tennis (Girls) | Cushing | Away | Win, 7-1 | |
| Apr 7 | Varsity Cycling (Coed) | East Coast Cycling Conference | Yale | ||
| Apr 5 | Varsity Baseball (Boys) | Greenfield HS | Home | Win, 5-1 | |
| Apr 4 | Junior Varsity Lacrosse (Boys) | Berkshire | Home | Win, 13-5 | |
| Apr 4 | Varsity Tennis (Boys) | Longmeadow | Home | Win, 6-1 | |
| Apr 4 | Junior Varsity Tennis (Boys) | Hotchkiss | Home | Loss, 5-2 | |
| Apr 4 | Varsity Lacrosse (Boys) | Berkshire | Home | Win, 8-6 | |
| Apr 4 | Junior Varsity Lacrosse (Girls) | St. Mark's (S) | Away | Loss, 7-5 | |
| Apr 4 | Varsity Lacrosse (Girls) | St. Mark's | Away | Loss, 17-4 | |
| Apr 4 | Junior Varsity Baseball (Boys) | Loomis (S) | Away | ||
| Apr 4 | Varsity Baseball (Boys) | Loomis | Away | Loss, 11-3 | |
| Apr 4 | Varsity Softball (Girls) | Cushing | Away | Loss, 10-1 | |
| Apr 4 | Varsity Water Polo (Girls) | Suffield | Away | Win, 13-7 | |
| Apr 4 | Varsity Tennis (Girls) | Kingswood (S) | Away | ||
| Apr 2 | Varsity Softball (Girls) | Frontier HS Scrimmage | Away | ||
| Apr 2 | Varsity Baseball (Boys) | Frontier HS | Away | Win, 3-1 | |
| Apr 1 | Varsity Tennis (Boys) | Kingswood Tournament | Away | 5th place | |
| Date | Sport | Opponent | Venue | Result | |
| Mar 31 | Varsity Lacrosse (Boys) | Brunswick | Home | Win, 7-6 (OT) | |
| Mar 31 | Varsity Water Polo (Girls) | Exeter | Away | Loss, 11-8 | |
| Mar 31 | Junior Varsity Lacrosse (Boys) | Brunswick | Home | Loss, 11-4 | |
| Mar 31 | Varsity Baseball (Boys) | Springfield College | CANCELLED | ||
| Mar 31 | Varsity Lacrosse (Girls) | New Canaan Playday | CANCELLED | ||
| Mar 31 | Varsity Tennis (Boys) | Kingswood Tournament | Away | ||
| Mar 28 | Varsity Lacrosse (Boys) | Navy Prep (S) | Home | ||
| Mar 28 | Varsity Baseball (Boys) | Groton | Home | Loss, 5-1 | |
| Mar 28 | Varsity Tennis (Boys) | Groton | Away | Win, 6 1/2 - 1/2 | |
| Mar 3 | Varsity Swimming & Diving (Girls) | New England's | Exeter | 2nd Place | |
| Mar 3 | Varsity Swimming & Diving (Boys) | New England's | Exeter | 2nd Place | |
| Date | Sport | Opponent | Venue | Result | |
| Feb 29 | Freshman Sophomore Cross Country (Boys) | --- | Andover (Phillips) | ||
| Feb 25 | Varsity Hockey (Boys) | Westminster | Home | Loss, 4-1 | |
| Feb 25 | Varsity Hockey (Girls) | Loomis | Home | Loss, 4-0 | |
| Feb 25 | Junior Varsity Hockey (Boys) | Westminster | Away | Loss, 3-2 | |
| Feb 25 | Varsity Basketball (Girls) | Berkshire | Away | Loss | |
| Feb 25 | Junior Varsity Basketball (Boys) | Hyde (CT) | Away | Win, 36-27 | |
| Feb 25 | Junior Varsity Hockey (Girls) | Loomis | Home | Win, 4-0 | |
| Feb 25 | Varsity Swimming & Diving (Boys) | Easterns/Westerns | Hopkins School | 1st Place | |
| Feb 25 | Varsity Squash (Girls) | New England's | Groton | ||
| Feb 25 | Varsity Squash (Boys) | New England's | Exeter | ||
| Feb 25 | Varsity Wrestling (Boys) | Nationals | Lehigh PA | ||
| Feb 25 | Varsity Swimming & Diving (Girls) | Easterns/Westerns | Hopkins School | First Place | |
| Feb 24 | Varsity Basketball (Boys) | Choate | Home | Win, 50-44 | |
| Feb 24 | Junior Varsity Basketball (Boys) | Choate | Home | Loss, 48-44 | |
| Feb 24 | Varsity Basketball (Girls) | Choate | Home | Loss, 39-35 | |
| Feb 22 | Reserve Squash (Boys) | Bement | Home | Win, 7-1 | |
| Feb 22 | Freshman Sophomore Basketball (Boys) | Loomis | Away | Loss, 51-41 | |
| Feb 22 | Junior Varsity Basketball (Girls) | Westminster | Home | Win, 31-24 | |
| Feb 22 | Reserve Squash (Girls) | Bement | Home | Win, 9-5 | |
| Feb 22 | Varsity Basketball (Boys) | Andover | Away | Loss, 59-41 | |
| Feb 22 | Varsity Squash (Girls) | Choate | Away | Win, 7-0 | |
| Feb 22 | Junior Varsity Basketball (Boys) | Brattleboro HS | Away | Loss, 43-33 | |
| Feb 22 | Varsity Squash (Boys) | Choate | Away | Loss, 7-0 | |
| Feb 22 | Varsity Hockey (Boys) | Kent | Home | Tie, 2-2 | |
| Feb 22 | Junior Varsity Squash (Girls) | Choate | Home | Win, 7-2 | |
| Feb 22 | Junior Varsity Squash (Boys) | Choate | Home | Loss, 7-0 | |
| Feb 22 | Varsity Alpine Skiing (Coed) | M.I.S.L. | Eaglebrook | Girls: 1st Boys: 1st | |
| Feb 22 | Varsity Basketball (Girls) | Westminster | Home | Win, 51-31 | |
| Feb 22 | Varsity Hockey (Girls) | Williston | Away | Loss, 6-2 | |
| Feb 22 | Junior Varsity Hockey (Girls) | NMH | CANCELLED | ||
| Feb 22 | Junior Varsity Hockey (Boys) | NMH | Home | Win, 3-2 | |
| Feb 18 | Junior Varsity Squash (Girls) | Exeter | Home | Win, 6-1 | |
| Feb 18 | Junior Varsity Squash (Boys) | Exeter | Home | Loss, 7-0 | |
| Feb 18 | Varsity Hockey (Boys) | Exeter | Away | Loss, 5-2 | |
| Feb 18 | Junior Varsity Basketball (Boys) | Eaglebrook | Away | Loss, 56-38 | |
| Feb 18 | Varsity Squash (Girls) | Exeter | Home | Win, 7-0 | |
| Feb 18 | Varsity Squash (Boys) | Exeter | Home | Win, 4-3 | |
| Feb 18 | Varsity Swimming & Diving (Girls) | Loomis | Away | Win | |
| Feb 18 | Varsity Hockey (Girls) | Hotchkiss | Home | Win, 3-2 | |
| Feb 18 | Varsity Swimming & Diving (Boys) | Loomis | Away | Win, 102-79 | |
| Feb 18 | Junior Varsity Basketball (Girls) | NMH | Home | Loss, 40-20 | |
| Feb 18 | Varsity Basketball (Girls) | NMH | Home | Loss, 44-29 | |
| Feb 18 | Varsity Basketball (Boys) | Tabor | Away | Loss, 76-66 | |
| Feb 18 | Junior Varsity Hockey (Girls) | Hotchkiss | Home | Tie, 3-3 | |
| Feb 18 | Freshman Sophomore Basketball (Boys) | Choate | Home | Win, 44-40 | |
| Feb 18 | Reserve Squash (Girls) | Andover and Choate | Home | Win, 5-2 (PA), 4-3 (CRH) | |
| Feb 18 | Junior Varsity Hockey (Boys) | NE Stars | CANCELLED | ||
| Feb 18 | Junior Varsity Swimming & Diving (Coed) | Eaglebrook Invitational | CANCELLED | ||
| Feb 18 | Varsity Wrestling (Boys) | New England's | NMH | ||
| Feb 17 | Varsity Hockey (Boys) | Williston | Home | Loss, 3-1 | |
| Feb 15 | Varsity Basketball (Girls) | Wilbraham | Away | Win, 46-36 | |
| Feb 15 | Varsity Hockey (Boys) | Taft | Away | Win, 6-4 | |
| Feb 15 | Reserve Squash (Boys) | Choate | Away | Win, 8-2 | |
| Feb 15 | Varsity Basketball (Boys) | Suffield | Away | Loss, 69-64 | |
| Feb 15 | Reserve Squash (Girls) | Suffield | Away | Loss, 6-1 v Suffield JV | |
| Feb 15 | Varsity Hockey (Girls) | Cushing | Home | Loss, 3-0 | |
| Feb 15 | Junior Varsity Basketball (Girls) | Wilbraham | Away | Loss, 31-26 | |
| Feb 15 | Junior Varsity Basketball (Boys) | NMH | Home | Loss, 62-27 | |
| Feb 15 | Junior Varsity Hockey (Boys) | NMH | Away | Loss, 4-3 | |
| Feb 15 | Freshman Sophomore Basketball (Boys) | NMH | Home | Loss, 50-38 | |
| Feb 15 | Varsity Alpine Skiing (Coed) | New England's | Proctor | Girls: 1st Boys: 1st | |
| Feb 14 | Junior Varsity Swimming & Diving (Coed) | Eaglebrook | CANCELLED | ||
| Feb 13 | Junior Varsity Squash (Girls) | Loomis | Away | Win, 8-0 | |
| Feb 13 | Varsity Basketball (Boys) | Frontier HS | Home | ||
| Feb 11 | Varsity Basketball (Girls) | Loomis | Away | Win, 41-37 | |
| Feb 11 | Junior Varsity Basketball (Girls) | Loomis | Away | Loss, 32-27 | |
| Feb 11 | Junior Varsity Hockey (Boys) | Avon | Home | Loss, 5-0 | |
| Feb 11 | Varsity Hockey (Girls) | Berkshire | Away | Tie, 1-1 | |
| Feb 11 | Varsity Squash (Boys) | Taft | Home | Loss, 7-0 | |
| Feb 11 | Varsity Swimming & Diving (Boys) | Hotchkiss | Home | Win, 98-76 | |
| Feb 11 | Freshman Sophomore Basketball (Boys) | Suffield | Home | Loss, 39-34 | |
| Feb 11 | Junior Varsity Squash (Boys) | Taft | Home | Win, 4-3 | |
| Feb 11 | Varsity Swimming & Diving (Girls) | Hotchkiss | Home | Win, 100 - 70 | |
| Feb 11 | Varsity Hockey (Boys) | Avon | Home | Win, 4-3 | |
| Feb 11 | Junior Varsity Basketball (Boys) | Exeter | Home | Loss, 44-25 | |
| Feb 11 | Varsity Basketball (Boys) | Exeter | Home | Loss, 66-56 | |
| Feb 11 | Junior Varsity Squash (Girls) | Taft | Away | ||
| Feb 11 | Junior Varsity Hockey (Girls) | Choate | Away | Tie | |
| Feb 11 | Reserve Squash (Boys) | Suffield | Home | Loss, 7-3 | |
| Feb 11 | Varsity Squash (Girls) | Greenwich & Taft | Taft | ||
| Feb 11 | Varsity Wrestling (Boys) | Class A Championships | Hyde (ME) | ||
| Feb 10 | Varsity Hockey (Girls) | St. Paul's | Home | Win, 5-3 | |
| Feb 8 | Varsity Hockey (Girls) | Westminster | Away | Loss, 4-2 | |
| Feb 8 | Varsity Hockey (Boys) | Loomis | Home | Win, 4-1 | |
| Feb 8 | Junior Varsity Basketball (Girls) | Suffield | Away | Win, 38-17 | |
| Feb 8 | Junior Varsity Swimming & Diving (Coed) | Bement | Home | ||
| Feb 8 | Reserve Squash (Boys) | Bement | Home | Win, 8-1 | |
| Feb 8 | Reserve Squash (Girls) | Bement | Home | Win, 4-1 | |
| Feb 8 | Varsity Basketball (Boys) | Taft | Home | Loss, 67-66 | |
| Feb 8 | Junior Varsity Basketball (Boys) | Taft | Home | Loss, 44-39 | |
| Feb 8 | Varsity Squash (Boys) | Avon | Away | Win, 6-1 | |
| Feb 8 | Varsity Alpine Skiing (Coed) | M.I.S.L. | Berkshire East | Girls: 1st Boys: 1st | |
| Feb 8 | Varsity Swimming & Diving (Boys) | Williston | CANCELLED | ||
| Feb 8 | Varsity Basketball (Girls) | Suffield | Away | Loss, 60-39 | |
| Feb 8 | Junior Varsity Squash (Boys) | Avon | Away | Win, 7-0 | |
| Feb 8 | Freshman Sophomore Basketball (Boys) | Williston | Away | Loss, 54-47 (OT) | |
| Feb 8 | Junior Varsity Squash (Girls) | Miss Porter's | Home | ||
| Feb 8 | Varsity Swimming & Diving (Girls) | Williston | CANCELLED | ||
| Feb 8 | Junior Varsity Hockey (Boys) | Loomis | Home | Win, 2-1 | |
| Feb 8 | Junior Varsity Hockey (Girls) | Williston | Away | Win, 5-3 | |
| Feb 3 | Varsity Squash (Girls) | Nationals | Choate | Win, Second in Nation | |
| Feb 3 | Varsity Squash (Boys) | Nationals | Choate | 6th place | |
| Feb 1 | Varsity Squash (Boys) | Brunswick and Belmont Hill | Home | Loss, 7-0. 7-0 | |
| Feb 1 | Varsity Wrestling (Boys) | Wilbraham & Worcester | Home | 48-30 (win v Wilbraham), 36-30 (loss v. Worcester) | |
| Feb 1 | Varsity Basketball (Girls) | KUA | Away | Loss, 42-35 | |
| Feb 1 | Reserve Squash (Girls) | Williston | Away | Win, 4-3 | |
| Feb 1 | Varsity Hockey (Boys) | Andover | Away | Loss, 5-2 | |
| Feb 1 | Junior Varsity Hockey (Boys) | Cardigan | Away | Loss, 10-0 | |
| Feb 1 | Varsity Alpine Skiing (Coed) | M.I.S.L. | Berkshire East | Girls: 2nd Boys: 1st | |
| Feb 1 | Freshman Sophomore Basketball (Boys) | Eaglebrook | Away | Win, 48-23 | |
| Feb 1 | Junior Varsity Squash (Boys) | Eaglebrook | Home | Win, 4-3 | |
| Feb 1 | Junior Varsity Basketball (Boys) | Wilbraham | Home | Loss, 48-31 | |
| Feb 1 | Junior Varsity Squash (Girls) | Williston | Away | Win, 9-1 | |
| Feb 1 | Junior Varsity Basketball (Girls) | Stoneleigh | Away | Win, 33-10 | |
| Date | Sport | Opponent | Venue | Result | |
| Jan 28 | Varsity Basketball (Boys) | Williston | Away | Win, 70-48 | |
| Jan 28 | Varsity Hockey (Boys) | Hotchkiss | Home | Loss, 5-2 | |
| Jan 28 | Varsity Squash (Boys) | Salisbury | Home | Win, 7-0 | |
| Jan 28 | Junior Varsity Basketball (Boys) | Williston | Away | Loss, 40-39 (OT) | |
| Jan 28 | Varsity Swimming & Diving (Boys) | Andover | Home | Loss, 89-96 | |
| Jan 28 | Varsity Swimming & Diving (Girls) | Andover | Home | Loss, 111-75 | |
| Jan 28 | Varsity Hockey (Girls) | Andover | Away | Win, 3-0 | |
| Jan 28 | Varsity Basketball (Girls) | Hotchkiss | Home | Loss, 55-45 | |
| Jan 28 | Junior Varsity Basketball (Girls) | Hotchkiss | Home | Loss, 35-28 | |
| Jan 28 | Junior Varsity Hockey (Girls) | Andover | Away | Tie, 2-2 | |
| Jan 28 | Junior Varsity Hockey (Boys) | Hotchkiss | Home | Win, 5-3 | |
| Jan 28 | Junior Varsity Squash (Girls) | St. Paul's | Home | Win, 6-1 | |
| Jan 28 | Varsity Squash (Girls) | St. Paul's | Home | Win, 6-1 | |
| Jan 28 | Varsity Wrestling (Boys) | Canterbury Quad | Away | Loss, 38-23 (Salisbury), 52-14 (Canterbury), 66-6 (CRH) | |
| Jan 28 | Freshman Sophomore Basketball (Boys) | Avon | Away | Win, 45-35 | |
| Jan 28 | Junior Varsity Squash (Boys) | Williston | Home | Win, 6-1 | |
| Jan 28 | Reserve Squash (Boys) | Williston | Home | Win, 8-1 | |
| Jan 25 | Junior Varsity Hockey (Boys) | Cathedral HS | Home | Win, 4-2 | |
| Jan 25 | Freshman Sophomore Basketball (Boys) | Loomis | Home | Loss, 66-29 | |
| Jan 25 | Varsity Hockey (Girls) | Pomfret | Away | Win, 2-0 | |
| Jan 25 | Varsity Hockey (Boys) | Westminster | Away | Win, 8-7 (OT) | |
| Jan 25 | Varsity Basketball (Boys) | Loomis | Away | Win, 50-36 | |
| Jan 25 | Junior Varsity Basketball (Boys) | Loomis | Away | Loss, 27-26 | |
| Jan 25 | Varsity Basketball (Girls) | New Hampton | Home | Loss, 40-21 | |
| Jan 25 | Junior Varsity Hockey (Girls) | Taft | Home | Win, 6-4 | |
| Jan 25 | Junior Varsity Squash (Girls) | Taft | Home | Win, 9-0 | |
| Jan 25 | Junior Varsity Basketball (Girls) | Choate | Home | Loss, 51-25 | |
| Jan 25 | Varsity Alpine Skiing (Coed) | M.I.S.L. | Berkshire East | Girls: 1st Boys: 1st | |
| Jan 25 | Junior Varsity Squash (Boys) | Westminster | Away | Win, 6-1 | |
| Jan 25 | Varsity Wrestling (Boys) | NMH | Home | Win, 32-12 (modified) | |
| Jan 25 | Varsity Squash (Boys) | Westminster | Away | Loss, 6-1 | |
| Jan 25 | Reserve Squash (Boys) | Suffield | Away | Loss, 6-1 | |
| Jan 25 | Varsity Swimming & Diving (Boys) | NMH | Away | Win, 95-71 | |
| Jan 25 | Varsity Swimming & Diving (Girls) | NMH | Away | Win, 114-56 | |
| Jan 23 | Varsity Squash (Girls) | Loomis | Home | Win, 7-0 | |
| Jan 21 | Varsity Hockey (Boys) | Choate | Away | Loss, 5-0 | |
| Jan 21 | Junior Varsity Hockey (Boys) | Choate | Away | CANCELLED | |
| Jan 21 | Varsity Basketball (Girls) | Andover | Away | Loss, 45-30 | |
| Jan 21 | Junior Varsity Hockey (Girls) | Choate | CANCELLED | ||
| Jan 21 | Reserve Squash (Girls) | Taft | CANCELLED | ||
| Jan 21 | Varsity Squash (Boys) | St. Paul's | Home | Win, 6-1 | |
| Jan 21 | Varsity Swimming & Diving (Boys) | Choate | CANCELLED | ||
| Jan 21 | Varsity Wrestling (Boys) | St. Paul's Tri | Away | ||
| Jan 21 | Varsity Swimming & Diving (Girls) | Choate | CANCELLED | ||
| Jan 21 | Junior Varsity Swimming & Diving (Coed) | NMH and Bement | NMH | ||
| Jan 21 | Junior Varsity Squash (Girls) | Westminster | CANCELLED | ||
| Jan 21 | Varsity Squash (Girls) | Westminster | CANCELLED | ||
| Jan 21 | Freshman Sophomore Basketball (Boys) | Andover | Away | ||
| Jan 21 | Varsity Basketball (Boys) | Andover | Home | Loss, 67-60 (OT) | |
| Jan 21 | Junior Varsity Basketball (Boys) | Andover | Home | Loss, 62-53 | |
| Jan 21 | Junior Varsity Basketball (Girls) | Andover | Away | Loss, 29-11 | |
| Jan 21 | Junior Varsity Squash (Boys) | St. Paul's | Home | Win, 7-0 | |
| Jan 21 | Varsity Hockey (Girls) | Taft | Away | Loss, 2-0 | |
| Jan 20 | Junior Varsity Squash (Girls) | Andover | Away | ||
| Jan 20 | Varsity Squash (Girls) | Andover | Away | Win, 6-1 | |
| Jan 20 | Varsity Hockey (Girls) | New Hampton | Home | Win, 5-3 | |
| Jan 18 | Junior Varsity Hockey (Boys) | Springfield Rifles | Home | Loss, 3-1 | |
| Jan 18 | Junior Varsity Hockey (Girls) | Loomis | Away | Win, 4-0 | |
| Jan 18 | Reserve Squash (Boys) | Choate | Away | Loss, 7-1 | |
| Jan 18 | Varsity Basketball (Boys) | Cushing | Away | Loss, 75-60 | |
| Jan 18 | Varsity Hockey (Boys) | KUA | Away | Loss, 6-3 | |
| Jan 18 | Varsity Basketball (Girls) | Williston | Home | Loss, 46-43 | |
| Jan 18 | Varsity Hockey (Girls) | Choate | Home | Win, 3-0 | |
| Jan 18 | Varsity Alpine Skiing (Coed) | M.I.S.L. | Berkshire East | Girls: 1st Boys: 1st | |
| Jan 18 | Junior Varsity Squash (Boys) | Choate | Away | Loss, 6-1 | |
| Jan 18 | Junior Varsity Basketball (Boys) | Cushing | Away | Win, 47-22 | |
| Jan 18 | Freshman Sophomore Basketball (Boys) | Cushing | Home | Loss, 26-20 | |
| Jan 18 | Junior Varsity Basketball (Girls) | Williston | Home | Loss, 35-29 | |
| Jan 14 | Junior Varsity Hockey (Boys) | Andover | Home | Win, 5-0 | |
| Jan 14 | Junior Varsity Squash (Boys) | Taft | Away | Loss, 3-4 | |
| Jan 14 | Freshman Sophomore Basketball (Boys) | Suffield | Away | Loss, 43-27 | |
| Jan 14 | Junior Varsity Basketball (Boys) | Worcester | Home | Loss, 55-50 | |
| Jan 14 | Junior Varsity Squash (Girls) | Westminster | Home | Win, 10-1 | |
| Jan 14 | Varsity Basketball (Boys) | Salisbury | Away | Loss, 63-52 | |
| Jan 14 | Varsity Hockey (Boys) | Trinity-Pawling | Home | Win, 4-2 | |
| Jan 14 | Varsity Squash (Boys) | Choate Tournament | Away | 2nd Place | |
| Jan 14 | Varsity Swimming & Diving (Girls) | Exeter | Away | Loss, 98-88 | |
| Jan 14 | Junior Varsity Hockey (Girls) | Exeter | Away | Win, 4-2 | |
| Jan 14 | Varsity Hockey (Girls) | Exeter | Away | Loss, 4-1 | |
| Jan 14 | Junior Varsity Basketball (Girls) | Exeter | Home | Loss, 21-17 | |
| Jan 14 | Varsity Basketball (Girls) | Exeter | Home | Win, 48-43 | |
| Jan 14 | Varsity Swimming & Diving (Boys) | Exeter | Away | Win, 110-76 | |
| Jan 14 | Reserve Squash (Girls) | Andover | Away | Win, 7-0 | |
| Jan 14 | Varsity Wrestling (Boys) | Andover Quint | Away | ||
| Jan 14 | Varsity Squash (Girls) | Choate Tournament | Away | 1st Place | |
| Jan 13 | Varsity Hockey (Boys) | Cushing | Away | Loss, 6-2 | |
| Jan 11 | Varsity Hockey (Boys) | Loomis | Away | Win, 4-1 | |
| Jan 11 | Junior Varsity Hockey (Boys) | Williston | Home | Loss, 4-2 | |
| Jan 11 | Junior Varsity Basketball (Girls) | Taft | Away | Win, 39-35 | |
| Jan 11 | Varsity Basketball (Girls) | Taft | Away | Loss, 59-36 | |
| Jan 11 | Junior Varsity Squash (Boys) | Andover | Away | Win, 7-0 | |
| Jan 11 | Varsity Wrestling (Boys) | Avon | Home | Loss, 67-9 | |
| Jan 11 | Varsity Squash (Boys) | Andover | Away | Win, 6-1 | |
| Jan 11 | Varsity Alpine Skiing (Coed) | M.I.S.L. | Berkshire East | Girls: 2nd Boys: 1st | |
| Jan 11 | Varsity Swimming & Diving (Girls) | Suffield | Away | Win, 103-83 | |
| Jan 11 | Varsity Basketball (Boys) | NMH | Home | Loss, 46-30 | |
| Jan 11 | Varsity Swimming & Diving (Boys) | Suffield | Away | Win, 96-90 | |
| Jan 11 | Junior Varsity Swimming & Diving (Coed) | NMH and Eaglebrook | Home | 2nd Place | |
| Jan 11 | Junior Varsity Hockey (Girls) | NMH | Home | Win, 7-0 | |
| Jan 11 | Varsity Hockey (Girls) | NMH | Away | Win, 2-0 | |
| Jan 11 | Junior Varsity Basketball (Boys) | NMH | Away | Loss, 90-49 | |
| Jan 9 | Varsity Squash (Boys) | Andover | Home | ||
| Jan 7 | Varsity Hockey (Boys) | Salisbury | Away | Loss, 4-1 | |
| Jan 7 | Freshman Sophomore Basketball (Boys) | Avon | Home | Loss, 52-26 | |
| Jan 7 | Varsity Squash (Girls) | Tabor | Home | Win, 7-0 | |
| Jan 7 | Varsity Basketball (Boys) | St. Paul's | Home | Win, 72-67 | |
| Jan 7 | Junior Varsity Hockey (Boys) | Salisbury | Away | Loss, 5-0 | |
| Jan 7 | Varsity Hockey (Girls) | Nobles | Away | Loss, 6-0 | |
| Jan 7 | Junior Varsity Basketball (Boys) | Avon | Away | Loss, 35-32 | |
| Jan 7 | Reserve Squash (Boys) | Williston | Away | Win, 7-0 | |
| Jan 7 | Varsity Squash (Boys) | Tabor | Away | Win, 7-0 | |
| Jan 7 | Junior Varsity Basketball (Girls) | Cushing | Home | Win, 31-16 | |
| Jan 7 | Varsity Wrestling (Boys) | Williston Quad | Away | 57-16 (loss v Suffield), 45-30 (win v Pomfret), 50-30 (loss v Williston | |
| Jan 7 | Junior Varsity Hockey (Girls) | Cushing | Away | Win, 7-1 | |
| Jan 7 | Reserve Squash (Girls) | Suffield | Home | Win, 4-3 | |
| Jan 6 | Varsity Hockey (Girls) | NE Falcons | Home | Win, 5-0 | |
| Jan 6 | Varsity Basketball (Boys) | Pomfret | Home | Win, 51-28 | |
| Jan 6 | Junior Varsity Basketball (Boys) | Brattleboro HS | Home | Loss, 55-48 | |
| Jan 6 | Varsity Basketball (Girls) | Vermont | Away | Win, 57-10 | |
| Jan 6 | Freshman Sophomore Basketball (Boys) | NMH | Away | Loss, 47-27 | |
| Jan 6 | Junior Varsity Hockey (Boys) | Academy St. Louis | Home | Loss, 4-1 | |
| Jan 4 | Varsity Hockey (Boys) | Pomfret | Home | Win, 6-1 | |
| Jan 4 | Varsity Basketball (Boys) | Cheshire | Home | Loss, 66-61 | |
| Jan 4 | Junior Varsity Basketball (Girls) | Marionapolis | Home | Loss, 39-16 | |
| Jan 4 | Varsity Squash (Boys) | Milton | Home | Loss, 6-1 | |
| Jan 4 | Junior Varsity Hockey (Boys) | Eaglebrook | Home | Win, 4-2 | |
| Jan 4 | Junior Varsity Squash (Boys) | Eaglebrook | Away | Win, 4-3 | |
| Jan 4 | Freshman Sophomore Basketball (Boys) | Eaglebrook | Home | Win, 35-16 | |
| Jan 4 | Varsity Basketball (Girls) | NMH | Away | Loss, 46-33 | |
| Date | Sport | Opponent | Venue | Result | |
| Dec 18 | Varsity Hockey (Boys) | Flood Marr Tournament | Away | Win, 2-1 (OT) Hotchkiss | |
| Dec 17 | Varsity Hockey (Girls) | Nichols | Deerfield Holiday Invitational | Loss, 3-1 | |
| Dec 17 | Varsity Basketball (Boys) | St. Paul's | Choate | Loss, 63-48 | |
| Dec 17 | Varsity Basketball (Girls) | NMH | Choate | Loss, 46-34 | |
| Dec 17 | Varsity Hockey (Boys) | Flood Marr Tournament | Away | Loss, 2-1 (OT v. Salisbury) | |
| Dec 16 | Varsity Hockey (Girls) | Stanstead | Deerfield Holiday Invitational | Loss, 6-3 | |
| Dec 16 | Varsity Basketball (Girls) | Lawrenceville | Choate | Loss, 53-35 | |
| Dec 16 | Varsity Basketball (Boys) | Choate | Choate | Loss, 60-40 | |
| Dec 16 | Varsity Hockey (Girls) | Wyoming Seminary | Deerfield Holiday Invitational | Win, 4-0 | |
| Dec 16 | Varsity Basketball (Girls) | Choate | Choate | Loss, 58-34 | |
| Dec 16 | Varsity Hockey (Boys) | Flood Marr Tournament | Away | 5-1 win (v. Milton) 2-1 loss (v. KUA) | |
| Dec 15 | Varsity Basketball (Boys) | Lawrenceville | Choate | Loss, 54-47 | |
| Dec 15 | Varsity Hockey (Girls) | Rothesay-Netherwood | Deerfield Holiday Invitational | Win, 5-3 | |
| Dec 14 | Junior Varsity Hockey (Boys) | Greenfield HS | Home | scrimmage | |
| Dec 14 | Junior Varsity Basketball (Girls) | Bement | Home | Win, 52-31 | |
| Dec 14 | Varsity Squash (Girls) | Groton | Away | Win, 7-0 | |
| Dec 14 | Junior Varsity Squash (Girls) | Groton | Away | Win, 7-0 | |
| Dec 14 | Varsity Swimming & Diving (Boys) | Minnechaug HS | Home | Win, 93-83 | |
| Dec 14 | Varsity Wrestling (Boys) | Loomis & Worcester | Worcester | Loss, LC 65 DA 15 | |
| Dec 14 | Varsity Hockey (Girls) | St. Mark's | Home | Win, 3-0 | |
| Dec 14 | Varsity Hockey (Boys) | Avon | Away | Loss, 8-2 | |
| Dec 14 | Varsity Basketball (Boys) | Avon | Away | Win, 54-51 | |
| Dec 14 | Freshman Sophomore Basketball (Boys) | Eagle Hill | Home | Win, 47-16 | |
| Dec 14 | Junior Varsity Basketball (Boys) | Suffield | Home | Win, 46-40 | |
| Dec 14 | Varsity Basketball (Girls) | Suffield Tournament | Suffield | Win, 51-25 (vs. Westminster) | |
| Dec 14 | Varsity Squash (Boys) | Loomis | Home | Win, 4-3 | |
| Dec 14 | Junior Varsity Squash (Boys) | Loomis | Home | Loss, 1-6 | |
| Dec 11 | Varsity Basketball (Girls) | TBD | Worcester | Loss, 69-32 (vs. Tilton) | |
| Dec 10 | Varsity Hockey (Boys) | Choate | Home | Loss, 3-1 | |
| Dec 10 | Varsity Basketball (Girls) | Worcester | Worcester | Loss, 45-32 | |
| Dec 10 | Varsity Hockey (Girls) | Kingswood | Away | Win, 3-0 | |
| Dec 10 | Junior Varsity Hockey (Boys) | Choate | Home | Win, 3-2 | |
| Dec 10 | Varsity Basketball (Boys) | Westminster | Home | Win, 61-50 | |
| Dec 10 | Varsity Wrestling (Boys) | Belmont Hill Quad | Away | ||
| Dec 10 | Junior Varsity Squash (Girls) | Loomis | Home | Win, 9-0 | |
| Dec 10 | Junior Varsity Basketball (Boys) | Westminster | Home | Loss, 35-33 | |
| Dec 10 | Junior Varsity Basketball (Girls) | NMH | Away | Loss, 29-10 | |
| Dec 10 | Junior Varsity Hockey (Girls) | Williston | Home | Win, 7-5 | |
| Dec 10 | Reserve Squash (Boys) | Eaglebrook | Away | Win, 4-3 | |
| Dec 10 | Varsity Squash (Girls) | Groton Invitational | Away | Win, 1st place | |
| Dec 10 | Junior Varsity Squash (Boys) | Williston | Away | Win, 4-3 | |
| Dec 10 | Freshman Sophomore Basketball (Boys) | Mini Tournament | Home | scrimmage | |
| Dec 9 | Junior Varsity Hockey (Boys) | Jr. Falcons | Home | Loss, 9-3 | |
| Dec 9 | Varsity Hockey (Boys) | Kingswood | Away | Win, 3-0 | |
| Dec 7 | Varsity Hockey (Boys) | NMH | Away | Loss, 2-0 | |
| Dec 7 | Freshman Sophomore Basketball (Boys) | Bement | Home | Win, 39-22 | |
| Dec 7 | Junior Varsity Hockey (Girls) | Westminster | Away | Tie, 2-2 | |
| Dec 7 | Junior Varsity Basketball (Boys) | Loomis | Home | Loss, 41-40 (OT) | |
| Dec 7 | Varsity Squash (Girls) | Milton | Home | Win, 7-0 | |
| Dec 7 | Junior Varsity Squash (Girls) | Milton | Home | Loss, 5-2 | |
| Dec 7 | Varsity Squash (Boys) | Groton | Away | Loss, 4-3 | |
| Dec 7 | Junior Varsity Squash (Boys) | Kingswood-Oxford | Away | Loss, 3-4 | |
| Dec 7 | Reserve Squash (Girls) | Miss Porter's | Away | Loss, 6-1 | |
| Dec 7 | Junior Varsity Basketball (Girls) | Miss Porter's | Home | ||
| Dec 7 | Varsity Basketball (Boys) | Loomis | Home | Win, 49-47 | |
| Dec 7 | Varsity Hockey (Girls) | Loomis | Away | Tie, 1-1 | |
| Dec 7 | Junior Varsity Hockey (Boys) | NMH | Home | Loss, 3-0 | |
| Dec 4 | Varsity Basketball (Girls) | Frontier Jamboree | Frontier Regional HS | scrimmage | |
| Dec 4 | Varsity Squash (Girls) | St.. George's | Home | Win, 6-1 | |
| Dec 3 | Varsity Basketball (Girls) | Navy Prep | Home | Loss, 53-44 | |
| Dec 3 | Varsity Hockey (Boys) | Groton | Home | Win, 6-0 | |
| Dec 3 | Varsity Swimming & Diving (Boys) | Milton | Away | Win, 93-64 | |
| Dec 3 | Varsity Swimming & Diving (Girls) | Milton | Away | Win, 95-77 | |
| Dec 3 | Varsity Squash (Boys) | Hotchkiss and Berkshire | Hotchkiss | 6-1 loss v Hotchkiss 6-1 win v Berkshire | |
| Dec 3 | Junior Varsity Squash (Boys) | Hotchkiss | Away | S | |
| Dec 3 | Varsity Basketball (Boys) | KUA | Away | Loss, 67-52 | |
| Dec 3 | Junior Varsity Squash (Girls) | Hotchkiss | Home | Win, 7-0 | |
| Dec 3 | Varsity Squash (Girls) | Hotchkiss and Taft | Home | Win, DA 5 v. Taft 2 and DA 7 v. Hotchkiss 0 | |
| Dec 3 | Junior Varsity Hockey (Boys) | Eaglebrook | Away | Loss, 3-0 | |
| Dec 3 | Varsity Hockey (Girls) | Ice Cats | Home | Win, 2-1 | |
| Dec 2 | Varsity Hockey (Girls) | Vermont | Home | Win, 4-3 | |
| Dec 1 | Varsity Basketball (Boys) | Frontier HS | CANCELLED | ||
| Date | Sport | Opponent | Venue | Result | |
| Nov 30 | Varsity Basketball (Boys) | Hotchkiss | Away | ||
| Nov 30 | Varsity Hockey (Boys) | Founders Jamboree | Hotchkiss | scrimmage | |
| Nov 16 | Varsity Field Hockey (Girls) | Westminster | Suffield | Loss, 1-2 | |
| Nov 16 | Varsity Volleyball (Girls) | St. Paul's | St. Paul's | ||
| Nov 12 | Junior Varsity Cross Country (Coed) | --- Interscholastics | Andover (Phillips) | ||
| Nov 12 | Varsity Cross Country (Boys) | --- Interscholastics | Andover (Phillips) | 2nd of 14 teams | |
| Nov 12 | Varsity Soccer (Girls) | Choate | Deerfield Academy | Loss, 3-0 | |
| Nov 12 | Varsity Football (Boys) | Choate | Deerfield Academy | Loss, 41-7 | |
| Nov 12 | Varsity Cross Country (Girls) | Multiple Teams - See Notes Interscholastics | Andover (Phillips) | 2nd | |
| Nov 12 | Varsity Field Hockey (Girls) | Choate | Deerfield Academy | Win, 4-1 | |
| Nov 12 | Varsity Soccer (Boys) | Choate | Deerfield Academy | Tie, 1-1 | |
| Nov 12 | Junior A Soccer (Boys) | Choate | Deerfield Academy | Tie, 1-1 | |
| Nov 12 | Junior Varsity Field Hockey (Girls) | Choate | Deerfield Academy | Win, 1-0 | |
| Nov 12 | Varsity Volleyball (Girls) | Choate | Deerfield Academy | Loss, 3-1 | |
| Nov 12 | Varsity Water Polo (Boys) | --- New England's Final Four | Exeter | Champions | |
| Nov 12 | Junior Varsity Football (Boys) | Choate | Deerfield Academy | Win, 22-21 | |
| Nov 12 | Junior Varsity Volleyball (Girls) | Choate | Deerfield Academy | Loss, 3-0 | |
| Nov 12 | Junior Varsity Soccer (Girls) | Choate | Deerfield Academy | Loss, 2-1 | |
| Nov 12 | Reserve Field Hockey (Girls) | Choate | Deerfield Academy | Tie, 0-0 | |
| Nov 12 | Reserve Soccer (Girls) | Choate | Deerfield Academy | Loss, 4-0 | |
| Nov 12 | Junior Varsity Soccer (Boys) | Choate | Deerfield Academy | Tie, 1-1 | |
| Nov 12 | Junior B Soccer (Boys) | Bement | Deerfield Academy | Loss, 3-0 | |
| Nov 9 | Varsity Volleyball (Girls) | Marionapolis | Deerfield Academy | Win, 3-1 | |
| Nov 9 | Varsity Water Polo (Boys) | Play-In Games DA vs. Andover | Deerfield Academy | Win, 9-3 | |
| Nov 9 | Junior Varsity Volleyball (Girls) | Marionapolis | Deerfield Academy | Win, 3-0 | |
| Nov 9 | Reserve Field Hockey (Girls) | Bement | Bement | Tie, 2-2 | |
| Nov 9 | Junior Varsity Football (Boys) | Eaglebrook | Eaglebrook | Win, 36-8 | |
| Nov 9 | Junior Varsity Water Polo (Boys) | Eaglebrook | Eaglebrook | Win, 9-8 | |
| Nov 9 | Junior Varsity Soccer (Girls) | Miss Hall's | Miss Hall's | Win, 4-1 | |
| Nov 9 | Junior A Soccer (Boys) | Putney | CANCELLED | ||
| Nov 9 | Reserve Soccer (Girls) | Loomis | Deerfield Academy | Win, 5-0 | |
| Nov 9 | Varsity Field Hockey (Girls) | Williston | Deerfield Academy | Loss, 0-2 | |
| Nov 9 | Varsity Soccer (Girls) | Wilbraham | Wilbraham | Loss, 6-3 | |
| Nov 9 | Junior Varsity Field Hockey (Girls) | Williston | Williston Northampton | Win, 2-0 | |
| Nov 9 | Varsity Soccer (Boys) | NMH | NMH | Loss, 4-1 | |
| Nov 9 | Junior Varsity Soccer (Boys) | Suffield | Deerfield Academy | Win, 3-1 | |
| Nov 9 | Junior B Soccer (Boys) | Cushing | Greenfield Community College | Loss, 3-0 | |
| Nov 7 | Varsity Soccer (Boys) | Loomis | Loomis Chaffee | Loss, 1-0 | |
| Nov 6 | Varsity Football (Boys) | Avon | Avon | Loss, 16-6 | |
| Nov 6 | Varsity Field Hockey (Girls) | Greenwich | Greenwich | Loss, 4-0 | |
| Nov 6 | Junior Varsity Field Hockey (Girls) | Greenwich | Greenwich | Loss, 8-0 | |
| Nov 6 | Varsity Soccer (Girls) | Hotchkiss | Hotchkiss | Win, 1-0 | |
| Nov 6 | Junior Varsity Soccer (Girls) | Hotchkiss | Hotchkiss | Win, 3-0 | |
| Nov 5 | Varsity Volleyball (Girls) | Taft | Taft | ||
| Nov 5 | Junior Varsity Volleyball (Girls) | Taft | Taft | ||
| Nov 5 | Varsity Cross Country (Boys) | NMH | NMH | Win, 24-33 | |
| Nov 5 | Junior Varsity Water Polo (Boys) | Choate | CANCELLED | ||
| Nov 5 | Junior Varsity Cross Country (Coed) | Multiple Teams - See Notes | NMH | ||
| Nov 5 | Varsity Soccer (Boys) | Williston | Deerfield Academy | Loss, 1-0 | |
| Nov 5 | Varsity Water Polo (Boys) | Suffield | CANCELLED | ||
| Nov 5 | Varsity Cross Country (Girls) | NMH Dual | Northfield | Win, 21-40 | |
| Nov 5 | Junior A Soccer (Boys) | Williston | Deerfield Academy | ||
| Nov 5 | Junior Varsity Soccer (Boys) | NMH | NMH | Tie, 1-1 | |
| Nov 5 | Junior Varsity Football (Boys) | Cardigan | Frontier Regional HS | Loss, 42-40 | |
| Nov 5 | Reserve Soccer (Girls) | Stoneleigh | Stoneleigh-Burnham | Win, 4-1 | |
| Nov 5 | Reserve Field Hockey (Girls) | Longmeadow | CANCELLED | ||
| Nov 4 | Reserve Soccer (Girls) | Bement | Deerfield Academy | Loss, 3-1 | |
| Nov 2 | Junior Varsity Water Polo (Boys) | Suffield | CANCELLED | ||
| Nov 2 | Junior Varsity Soccer (Boys) | Avon | CANCELLED | ||
| Nov 2 | Junior A Soccer (Boys) | Avon | CANCELLED | ||
| Nov 2 | Varsity Soccer (Boys) | Wilbraham | CANCELLED | ||
| Nov 2 | Varsity Field Hockey (Girls) | Sacred Heart | CANCELLED | ||
| Nov 2 | Junior B Soccer (Boys) | Bement | CANCELLED | ||
| Nov 2 | Varsity Soccer (Girls) | Suffield | CANCELLED | ||
| Nov 2 | Junior Varsity Soccer (Girls) | Suffield | CANCELLED | ||
| Date | Sport | Opponent | Venue | Result | |
| Oct 31 | Varsity Volleyball (Girls) | NMH | CANCELLED | ||
| Oct 31 | Junior Varsity Volleyball (Girls) | NMH | CANCELLED | ||
| Oct 29 | Junior Varsity Field Hockey (Girls) | Andover | CANCELLED | ||
| Oct 29 | Junior Varsity Cross Country (Coed) | Andover | Andover (Phillips) | ||
| Oct 29 | Junior Varsity Cross Country (Boys) | Andover | Andover (Phillips) | ||
| Oct 29 | Junior Varsity Water Polo (Boys) | Andover | CANCELLED | ||
| Oct 29 | Varsity Cross Country (Boys) | Andover | Andover (Phillips) | Loss, 28-29 | |
| Oct 29 | Varsity Football (Boys) | Andover | CANCELLED | ||
| Oct 29 | Varsity Volleyball (Girls) | Andover | CANCELLED | ||
| Oct 29 | Junior Varsity Volleyball (Girls) | Andover | CANCELLED | ||
| Oct 29 | Varsity Soccer (Boys) | Andover | CANCELLED | ||
| Oct 29 | Varsity Soccer (Girls) | Andover | CANCELLED | ||
| Oct 29 | Varsity Cross Country (Girls) | Andover Dual | Andover (Phillips) | Win, 21-34 | |
| Oct 29 | Varsity Field Hockey (Girls) | Andover | CANCELLED | ||
| Oct 29 | Junior Varsity Soccer (Boys) | Andover | CANCELLED | ||
| Oct 29 | Junior Varsity Football (Boys) | Andover | CANCELLED | ||
| Oct 29 | Junior Varsity Soccer (Girls) | Andover | CANCELLED | ||
| Oct 29 | Reserve Field Hockey (Girls) | Andover | CANCELLED | ||
| Oct 29 | Reserve Soccer (Girls) | Andover | CANCELLED | ||
| Oct 29 | Junior A Soccer (Boys) | Andover | CANCELLED | ||
| Oct 29 | Junior B Soccer (Boys) | Andover | CANCELLED | ||
| Oct 29 | Varsity Water Polo (Boys) | Andover | CANCELLED | ||
| Oct 28 | Reserve Soccer (Girls) | Hartsbrook | Deerfield Academy | ||
| Oct 26 | Junior Varsity Field Hockey (Girls) | Worcester | Worcester | Win, 2-0 | |
| Oct 26 | Junior Varsity Football (Boys) | Loomis | Eaglebrook | ||
| Oct 26 | Junior Varsity Water Polo (Boys) | Loomis | Deerfield Academy | ||
| Oct 26 | Varsity Volleyball (Girls) | St. Paul's | St. Paul's | ||
| Oct 26 | Junior Varsity Volleyball (Girls) | St. Paul's | St. Paul's | ||
| Oct 26 | Varsity Soccer (Boys) | KUA | KUA | Loss, 5-2 | |
| Oct 26 | Varsity Field Hockey (Girls) | Worcester | Worcester | Win, 4-0 | |
| Oct 26 | Varsity Water Polo (Boys) | Loomis | Deerfield Academy | Win, 17-9 | |
| Oct 26 | Junior A Soccer (Boys) | Eaglebrook | Deerfield Academy | Loss, 3-7 | |
| Oct 26 | Junior B Soccer (Boys) | Williston | Williston Northampton | ||
| Oct 22 | Junior Varsity Water Polo (Boys) | Exeter | Deerfield Academy | Win, 11-5 | |
| Oct 22 | Varsity Cross Country (Boys) | Exeter | Deerfield Academy | Loss, 18-37 | |
| Oct 22 | Varsity Football (Boys) | Exeter | Frontier Regional HS | Loss, 26-27 | |
| Oct 22 | Varsity Cross Country (Girls) | Exeter dual | Deerfield Academy | Win, 21-36 | |
| Oct 22 | Varsity Field Hockey (Girls) | Taft | Deerfield Academy | Win, 3-1 | |
| Oct 22 | Junior Varsity Cross Country (Coed) | Exeter | Deerfield Academy | ||
| Oct 22 | Varsity Volleyball (Girls) | Exeter | Deerfield Academy | Loss, 3-0 | |
| Oct 22 | Varsity Soccer (Boys) | Exeter | Deerfield Academy | Loss, 3-0 | |
| Oct 22 | Varsity Water Polo (Boys) | Exeter | Deerfield Academy | Loss, 8-2 | |
| Oct 22 | Junior Varsity Volleyball (Girls) | Exeter | Deerfield Academy | Loss, 3-1 | |
| Oct 22 | Junior Varsity Soccer (Boys) | Exeter | Greenfield Community College | Tie, 1-1 | |
| Oct 22 | Reserve Field Hockey (Girls) | Taft | CANCELLED | ||
| Oct 22 | Varsity Soccer (Girls) | Taft | Eaglebrook Track Field | Win, 4-2 | |
| Oct 22 | Junior Varsity Soccer (Girls) | Taft | Greenfield Community College | Win, 7-2 | |
| Oct 22 | Junior Varsity Field Hockey (Girls) | Taft | Frontier Regional HS | Win, 1-0 | |
| Oct 22 | Reserve Soccer (Girls) | Westminster | Deerfield Academy | Win, 4-1 | |
| Oct 22 | Junior Varsity Football (Boys) | Cathedral HS | Eaglebrook | Win, 30-6 | |
| Oct 22 | Junior A Soccer (Boys) | Belchertown | Greenfield Community College | Loss, 2-0 | |
| Oct 22 | Junior B Soccer (Boys) | Eaglebrook | Eaglebrook Uppvall Field | Loss, 4-2 | |
| Oct 20 | Reserve Soccer (Girls) | Bement | Deerfield Academy | Win, 2-1 | |
| Oct 19 | Reserve Field Hockey (Girls) | Westminster | CANCELLED | ||
| Oct 19 | Junior Varsity Water Polo (Boys) | Williston | Deerfield Academy | Win, 7-4 | |
| Oct 19 | Junior Varsity Field Hockey (Girls) | Westminster | CANCELLED | ||
| Oct 19 | Junior B Soccer (Boys) | PVPA | CANCELLED | ||
| Oct 19 | Varsity Soccer (Boys) | Loomis | CANCELLED | ||
| Oct 19 | Junior Varsity Soccer (Boys) | Loomis | CANCELLED | ||
| Oct 19 | Junior A Soccer (Boys) | Westminster | CANCELLED | ||
| Oct 19 | Varsity Volleyball (Girls) | Ethel Walker | Deerfield Academy | Win, 3-1 | |
| Oct 19 | Varsity Field Hockey (Girls) | Westminster | Deerfield Academy | Loss, 2-4 | |
| Oct 19 | Varsity Water Polo (Boys) | Williston | Deerfield Academy | Win, 15-4 | |
| Oct 19 | Varsity Soccer (Girls) | Cushing | CANCELLED | ||
| Oct 19 | Junior Varsity Volleyball (Girls) | Ethel Walker | Deerfield Academy | ||
| Oct 19 | Junior Varsity Soccer (Girls) | Cushing | CANCELLED | ||
| Oct 15 | Junior Varsity Cross Country (Coed) | Loomis and Choate | Loomis Chaffee | ||
| Oct 15 | Varsity Cross Country (Boys) | Loomis and Choate | Loomis Chaffee | Win, 2 Wins | |
| Oct 15 | Varsity Football (Boys) | Loomis | Loomis Chaffee | Loss, 21-27 | |
| Oct 15 | Varsity Cross Country (Girls) | Loomis and Choate Tri meet | Loomis Chaffee | Win, 27-28 | |
| Oct 15 | Varsity Water Polo (Boys) | Hotchkiss | Hotchkiss | Win, 13-4 | |
| Oct 15 | Junior Varsity Soccer (Boys) | Hotchkiss | Hotchkiss | Win, 4-1 | |
| Oct 15 | Junior A Soccer (Boys) | Hotchkiss | Hotchkiss | Tie, 2-2 | |
| Oct 15 | Reserve Soccer (Girls) | Loomis | Loomis Chaffee | Tie, 1-1 | |
| Oct 15 | Varsity Volleyball (Girls) | Amherst HS | Deerfield Academy | Loss, 2-3 | |
| Oct 15 | Varsity Soccer (Girls) | Loomis | Loomis Chaffee | Loss, 3-0 | |
| Oct 15 | Junior Varsity Volleyball (Girls) | Amherst HS | Deerfield Academy | Win, 3-1 | |
| Oct 15 | Junior Varsity Field Hockey (Girls) | Loomis | Loomis Chaffee | Loss, 0-1 | |
| Oct 15 | Junior Varsity Soccer (Girls) | Loomis | Loomis Chaffee | Win, 3-2 | |
| Oct 15 | Reserve Field Hockey (Girls) | Loomis | Loomis Chaffee | Win, 2-0 | |
| Oct 15 | Junior Varsity Football (Boys) | Cushing | Cushing | Win, 28-12 | |
| Oct 15 | Varsity Field Hockey (Girls) | Loomis | Loomis Chaffee | Win, 2-0 | |
| Oct 15 | Junior B Soccer (Boys) | Eaglebrook | Eaglebrook | Loss, 11-1 | |
| Oct 14 | Varsity Soccer (Boys) | Hotchkiss | Hotchkiss | Loss, 3-0 | |
| Oct 12 | Varsity Field Hockey (Girls) | KUA | Kimball Union | Win, 2-0 | |
| Oct 12 | Varsity Soccer (Boys) | Westminster | Deerfield Academy | Tie, 1-1 | |
| Oct 12 | Junior Varsity Soccer (Boys) | Westminster | Greenfield Community College | 2-2 | |
| Oct 12 | Junior Varsity Water Polo (Boys) | Wilbraham | Wilbraham | Loss, 16-15 OT | |
| Oct 12 | Junior A Soccer (Boys) | Suffield | Suffield | Loss, 3-2 | |
| Oct 12 | Reserve Soccer (Girls) | Vermont | Vermont | Win, 6-1 | |
| Oct 12 | Varsity Volleyball (Girls) | NMH | NMH | Loss, 1-3 | |
| Oct 12 | Junior Varsity Volleyball (Girls) | NMH | NMH | Win, 3-1 | |
| Oct 12 | Junior Varsity Soccer (Girls) | NMH | NMH | Win, 4-1 | |
| Oct 12 | Varsity Soccer (Girls) | NMH | Deerfield Academy | Win, 3-2 | |
| Oct 12 | Junior Varsity Field Hockey (Girls) | NMH | Deerfield Academy | Win, 4-1 | |
| Oct 8 | Varsity Field Hockey (Girls) | Kent | Deerfield Academy | Win, 3-0 | |
| Oct 8 | Varsity Soccer (Girls) | Kent | Deerfield Academy | Win, 4-0 | |
| Oct 8 | Junior Varsity Field Hockey (Girls) | Kent | Frontier Regional HS | Win, 4-0 | |
| Oct 8 | Junior Varsity Soccer (Girls) | Kent | Greenfield Community College | Win, 5-0 | |
| Oct 8 | Junior Varsity Cross Country (Coed) | Trinity-Pawling | Trinity-Pawling | ||
| Oct 8 | Varsity Cross Country (Boys) | Trinity-Pawling | Trinity-Pawling | Win | |
| Oct 8 | Varsity Cross Country (Girls) | Berkshire | Deerfield Academy | Win, 2-0 | |
| Oct 8 | Varsity Soccer (Boys) | Avon | Avon | Win, 1-0 | |
| Oct 8 | Junior Varsity Soccer (Boys) | Wilbraham | Wilbraham | Win, 5-0 | |
| Oct 8 | Junior B Soccer (Boys) | Westminster | Westminster | Loss, 5-1 | |
| Oct 8 | Reserve Soccer (Girls) | NMH | NMH | Tie, 1-1 | |
| Oct 8 | Varsity Football (Boys) | Hotchkiss | Frontier Regional HS | Win, 42-21 | |
| Oct 8 | Varsity Water Polo (Boys) | Malvern | CANCELLED | ||
| Oct 8 | Varsity Volleyball (Girls) | Hotchkiss | Deerfield Academy | Win, 3-2 | |
| Oct 8 | Junior Varsity Volleyball (Girls) | Hotchkiss | Deerfield Academy | Win, 3-0 | |
| Oct 8 | Junior Varsity Football (Boys) | Hotchkiss | Eaglebrook | Win, 36-8 | |
| Oct 8 | Reserve Field Hockey (Girls) | Longmeadow | Longmeadow Wolf Swamp Field | Loss, 5-1 | |
| Oct 5 | Junior Varsity Water Polo (Boys) | Choate | Choate | Win, 9-7 | |
| Oct 5 | Varsity Soccer (Girls) | Williston | Williston Northampton | Tie, 2-2 | |
| Oct 5 | Varsity Soccer (Boys) | Salisbury | Salisbury | Win, 2-0 | |
| Oct 5 | Junior Varsity Football (Boys) | Salisbury | Salisbury | Loss, 6-13 | |
| Oct 5 | Varsity Water Polo (Boys) | Choate | Choate | Loss, 11-10 OT | |
| Oct 5 | Junior A Soccer (Boys) | NMH | Deerfield Academy | Tie, 1-1 | |
| Oct 5 | Reserve Soccer (Girls) | Westminster | Westminster | Win, 5-0 | |
| Oct 5 | Varsity Volleyball (Girls) | Williston | Williston Northampton | Win, 3-1 | |
| Oct 5 | Junior Varsity Volleyball (Girls) | Williston | Williston Northampton | Win, 2-0 | |
| Oct 5 | Junior Varsity Field Hockey (Girls) | NMH | Northfield | Win, 4-0 | |
| Oct 5 | Junior Varsity Soccer (Girls) | Williston | Williston Northampton | Win, 5-0 | |
| Oct 5 | Varsity Field Hockey (Girls) | NMH | Northfield | Win, 2-1 | |
| Oct 5 | Junior Varsity Soccer (Boys) | NMH | Deerfield Academy | Win, 3-1 | |
| Oct 3 | Reserve Field Hockey (Girls) | Bement | Deerfield Academy | Win, 1-0 | |
| Oct 2 | Varsity Water Polo (Boys) | Multiple Teams - See Notes | Greenwich | Win | |
| Oct 1 | Varsity Cross Country (Girls) | Westminster Invitational | Westminster | Win, 8-0 | |
| Oct 1 | Varsity Cross Country (Boys) | Multiple Teams - See Notes Invitational | Westminster | Win, 1st Place | |
| Oct 1 | Junior Varsity Water Polo (Boys) | St. John's | Deerfield Academy | Win, 9-8 | |
| Oct 1 | Varsity Field Hockey (Girls) | Exeter | Deerfield Academy | Win, 2-1 | |
| Oct 1 | Varsity Soccer (Boys) | Kent | Kent | Loss, 1-2 | |
| Oct 1 | Junior Varsity Field Hockey (Girls) | Exeter | Frontier Regional HS | Win, 4-0 | |
| Oct 1 | Junior Varsity Soccer (Boys) | Kent | CANCELLED | ||
| Oct 1 | Varsity Soccer (Girls) | Pomfret | Pomfret | Loss, 5-1 | |
| Oct 1 | Varsity Football (Boys) | Taft | Taft | Loss, 6-49 | |
| Oct 1 | Junior Varsity Cross Country (Coed) | --- | Westminster | ||
| Oct 1 | Junior Varsity Soccer (Girls) | Pomfret | Pomfret | Win, 3-0 | |
| Oct 1 | Varsity Volleyball (Girls) | Hopkins | Hopkins School | Win, 3-0 | |
| Oct 1 | Junior Varsity Volleyball (Girls) | Hopkins | Hopkins School | Win, 3-1 | |
| Oct 1 | Reserve Soccer (Girls) | Taft | CANCELLED | ||
| Oct 1 | Varsity Water Polo (Boys) | St. John's | Deerfield Academy | Loss, 16-13 | |
| Oct 1 | Reserve Field Hockey (Girls) | NMH | CANCELLED | ||
| Oct 1 | Junior B Soccer (Boys) | Eaglebrook | Eaglebrook | Loss, 2-0 | |
| Date | Sport | Opponent | Venue | Result | |
| Sep 28 | Junior B Soccer (Boys) | PVPA | Deerfield Academy | Loss, 3-0 | |
| Sep 28 | Varsity Soccer (Girls) | Williams College | Williams College | ||
| Sep 28 | Junior Varsity Water Polo (Boys) | Suffield | Deerfield Academy | Win, 13-6 | |
| Sep 28 | Junior Varsity Field Hockey (Girls) | Ethel Walker | Deerfield Academy | Win, 2-0 | |
| Sep 28 | Varsity Soccer (Boys) | Taft | Deerfield Academy | Loss, 1-2 | |
| Sep 28 | Varsity Volleyball (Girls) | Loomis | Loomis Chaffee | Win, 3-1 | |
| Sep 28 | Junior Varsity Soccer (Boys) | Taft | Greenfield Community College | Win, 2-1 | |
| Sep 28 | Junior Varsity Volleyball (Girls) | Loomis | Loomis Chaffee | ||
| Sep 28 | Junior A Soccer (Boys) | Loomis | Loomis Chaffee | ||
| Sep 28 | Reserve Soccer (Girls) | NMH | NMH | Win, 3-0 | |
| Sep 28 | Varsity Water Polo (Boys) | Suffield | Deerfield Academy | Loss, 10-9 | |
| Sep 28 | Junior Varsity Soccer (Girls) | NMH | NMH | ||
| Sep 28 | Varsity Field Hockey (Girls) | Ethel Walker | Deerfield Academy | Win, 5-0 | |
| Sep 27 | Varsity Soccer (Girls) | Worcester | Deerfield Academy | Loss, 2-1 | |
| Sep 26 | Junior B Soccer (Boys) | Bement | Deerfield Academy | Loss, 4-1 | |
| Sep 24 | Varsity Cross Country (Girls) | Canterbury Invitational | Canterbury | Win, 15-0 | |
| Sep 24 | Reserve Field Hockey (Girls) | Hotchkiss | Hotchkiss | Loss, 5-1 | |
| Sep 24 | Junior Varsity Field Hockey (Girls) | Hotchkiss | Hotchkiss | Loss, 1-2 | |
| Sep 24 | Junior A Soccer (Boys) | Taft | Eaglebrook | Tie, 1-1 | |
| Sep 24 | Varsity Cross Country (Boys) | --- Invitational | Canterbury | 2nd Place | |
| Sep 24 | Varsity Soccer (Girls) | Exeter | Exeter | Loss, 3-0 | |
| Sep 24 | Junior Varsity Football (Boys) | Avon | Avon | Loss, 20-35 | |
| Sep 24 | Junior Varsity Soccer (Girls) | Exeter | Exeter | Win, 5-0 | |
| Sep 24 | Varsity Soccer (Boys) | Brunswick | Deerfield Academy | Loss, 1-2 | |
| Sep 24 | Varsity Field Hockey (Girls) | Hotchkiss | Hotchkiss | Loss, 0-4 | |
| Sep 24 | Varsity Football (Boys) | NMH | NMH | Win, 21-14 | |
| Sep 24 | Junior B Soccer (Boys) | Williston | Deerfield Academy | Loss, 4-0 | |
| Sep 24 | Reserve Soccer (Girls) | Stoneleigh | Deerfield Academy | Win, 5-0 | |
| Sep 24 | Varsity Water Polo (Boys) | Hopkins and PA | Williston Northampton | Win, 9-3, 12-4 | |
| Sep 23 | Junior Varsity Water Polo (Boys) | Eaglebrook | Deerfield Academy | Win, 11-7 | |
| Sep 23 | Varsity Soccer (Boys) | Worcester | Deerfield Academy | Tie, 1-1 | |
| Sep 21 | Varsity Soccer (Girls) | Westminster | Deerfield Academy | Tie, 4-4 | |
| Sep 21 | Junior Varsity Water Polo (Boys) | Loomis | Loomis Chaffee | Loss, 6-12 | |
| Sep 21 | Varsity Volleyball (Girls) | Worcester | Deerfield Academy | Win, 3-2 | |
| Sep 21 | Varsity Field Hockey (Girls) | Pomfret | Pomfret | Win, 3-0 | |
| Sep 21 | Junior Varsity Volleyball (Girls) | Worcester | Deerfield Academy | Win, 5-0 | |
| Sep 21 | Junior A Soccer (Boys) | Cardigan | Cardigan Mountain | Loss, 0-3 | |
| Sep 21 | Junior Varsity Football (Boys) | Frontier HS Scrimmage | Frontier HS | ||
| Sep 21 | Junior Varsity Soccer (Girls) | Westminster | Westminster | Win, 4-0 | |
| Sep 21 | Reserve Soccer (Girls) | Miss Porter's | Miss Porter's School | Win, 4-2 | |
| Sep 21 | Varsity Water Polo (Boys) | Loomis | Loomis Chaffee | Loss, 10-11 | |
| Sep 21 | Junior Varsity Field Hockey (Girls) | Vermont | Deerfield Academy | Loss, 0-3 | |
| Sep 21 | Varsity Soccer (Boys) | Suffield | Deerfield Academy | Loss, 1-2 | |
| Sep 17 | Varsity Cross Country (Boys) | Multiple Teams - See Notes Invitational | Northfield Mount Hermon | No Scores | |
| Sep 17 | Varsity Water Polo (Boys) | Choate | Deerfield Academy | Win, 6-4 | |
| Sep 17 | Varsity Cross Country (Girls) | Multiple Teams - See Notes Invitational | NMH | ||
| Sep 17 | Junior A Soccer (Boys) | Vermont | Deerfield Academy | Tie, 2-2 | |
| Sep 17 | Varsity Soccer (Girls) | Milton | Milton | Win, 2-1 | |
| Sep 17 | Varsity Field Hockey (Girls) | Berkshire | Berkshire | Tie, 1-1 | |
| Sep 17 | Junior Varsity Soccer (Boys) | Suffield | Suffield | Win, 6-0 | |
| Sep 17 | Junior Varsity Soccer (Girls) | Vermont | Deerfield Academy | Loss, 0-2 | |
| Sep 17 | Junior Varsity Cross Country (Coed) | Multiple Teams - See Notes Invitational | NMH | ||
| Sep 17 | Varsity Football (Boys) | Salisbury Scrimmage | Salisbury | ||
| Sep 17 | Varsity Water Polo (Boys) | Brunswick | Deerfield Academy | Win, 6-4, 13-5 | |
| Sep 17 | Varsity Soccer (Boys) | Williams | Williams College | Loss, 0-1 | |
| Sep 14 | Varsity Soccer (Boys) | Berkshire Scrimmage | Berkshire | Tie, 4-4 | |
| Sep 14 | Varsity Soccer (Girls) | Brooks Scrimmage | Lawrence | Loss, 1-3 | |
| Sep 14 | Varsity Football (Boys) | Cushing Scrimmage | Cushing | ||
| Sep 14 | Varsity Volleyball (Girls) | --- Playday | Loomis Chaffee | ||
| Sep 10 | Varsity Field Hockey (Girls) | --- Playday | Deerfield Academy | ||
| Sep 10 | Varsity Soccer (Boys) | Vermont | Vermont | ||
| Sep 10 | Varsity Soccer (Girls) | --- Playday | NMH | ||