Cheshire Academy competes in the New England Preparatory School Athletic Council (NEPSAC) Class C Division. The Cats reached their first NEPSAC tournament in school history and won the inaugural New England Girls Basketball League title in 2017-2018.

The Cats play a competitive 20-plus game schedule with home games played at Arthur Sheriff Field House. Over the years, student-athletes have gone on to play at the collegiate level and even professionally. The program accommodates student-athletes of all skill levels, and focuses on skill development, teamwork, and college placement.