Cheshire Academy plays in the highly competitive New England Preparatory School Athletic Council (NEPSAC) Class B Division, which prepares student-athletes for collegiate soccer. CA plays a very competitive and robust schedule against some of the other top prep programs in the region. The Cats have produced over 40 all-league players in recent years and student-athletes have gone on to play in various collegiate programs.

Home games are played on Simosa Field. There is also a junior varsity team to develop players through fundamental skills and fitness.