Cheshire Academy has a rich history of success on the football field and has established itself as one of the top prep football programs in New England. In 2023, the varsity football team was won the NEPSAC Drew Gamere Bowl championship.

The program prides itself in its ability to prepare players to not only have successful high school careers, but also the ability to compete at the collegiate level. Cheshire Academy has produced well over 100 college football players in the last decade. Those players have gone on to play at countless collegiate programs, ranging from the SEC to the Ivy League and NESCAC.

The Cats play a highly competitive schedule in the new Northeast Prep Football Conference. The football team plays home games on Simosa Field and student-athletes also have access to the school’s Simosa Strength and Conditioning Room. Cheshire Academy also fields a junior varsity football team