Deerfield's baseball tradition is rooted in consistency. Since the establishment of the Central New England Prep School Baseball League (CNEPSBL) 26 years ago, Deerfield reached the postseason 20 times. In 2009, Deerfield, seeded fourth in the tournament after ending with an 8-4 league record, won the CNEPSBL championship, defeating two strong and well-coached teams from Worcester Academy and Phillips Andover Academy. It was Deerfield Academy's fourth championship and its first since 1997. Deerfield recorded an 11-6 overall slate, the most wins in over a decade. Deerfield has seen its share of players move on to collegiate careers. Big Green players can currently be found competing for Trinity College (CT), Colby, Bates, Babson, Bucknell, Middlebury, and Princeton.
Among Deerfield's more prominent baseball alums are Pete Varney ’67, who played both baseball and football at Harvard before signing on for a career with the Chicago White Sox, and Mike Trombley '86, who saw time with the Twins, Orioles, and Dodgers.
The Big Green opens every season during spring break by traveling to Fort Pierce, FL, for a week of spring training and games against national competition.
And when Deerfield's baseball teams return, they come home to one of the premier prep school baseball fields in all of New England. Headmaster's Field is a professional quality field, which was constructed with the help of Mark Actman, designer of Coors Field, home of the Colorado Rockies.