Cheshire Academy has seen consistent success on the court, reaching the NEPSAC Class B  playoffs 6 times in the last 8 years years.

The Cats play in the New England Preparatory School Athletic Council Class B Division against schools such as Canterbury, Kingswood-Oxford, and Suffield Academy. Home matches are played on the David Markin ’48 Tennis Courts (nine courts in all), which features the Harry G. Carpenter ’46 Pavilion.

In addition to helping strong players prepare for college play, the program also fields a junior varsity team and accommodates student-athletes of all skill levels.