Cheshire Academy competes in the New England Preparatory School Athletic Council (NEPSAC) Class AA Division, considered by many as one of the top prep basketball leagues in the nation. The program prepares student-athletes to be successful academically and athletically at Division I, II, and III college programs across the country. The Cats play a 25-plus game schedule, and its basketball alumni have gone on to play at all levels of college basketball and professionally.

Cheshire Academy emerged as a regional power on the hardwood in the early 1990s, producing several All-Americans and winning multiple titles during that era. Cheshire Academy reached the Class AA semifinals in 2015-2016 and won the Class B title in 2013-2014.

Cheshire Academy also fields junior varsity and thirds teams, allowing players at all skill levels the opportunity to play.