Cheshire Academy competes in the New England Preparatory School Athletic Council (NEPSAC) Class A Division, the highest division of the league. The Cats reached the postseason in each of the last three years and have a combined 34-4 regular season record during that span. They play a challenging schedule that includes programs such as Choate, Deerfield Academy and Brunswick.

The Cats have produced student-

Cheshire Academy competes in the New England Preparatory School Athletic Council (NEPSAC) Class B Division. The Cats have been regulars in post-season play in recent years. 

The Cats have produced many student-athletes who have gone on to play in college, most recently including Bates College, Villanova, NC State, UNC, Connecticut College and Trinity College. While the tennis program is suited for the aspiring college tennis player, it’s also a good fit for the student-athlete who plays recreationally. 

Home matches are played on the David Markin ’48 Tennis Courts (nine courts in all), which features the Harry G. Carpenter ’46 Pavilion.

The Cats have a rich tennis history. In the late 1920s, two Cheshire Academy roommates – Sidney Wood and Frank Shields – were destined to meet in the Wimbledon Men’s final a few years later. In the late 1940s, some very strong teams were led by future United States Tennis Association president David Markin.