Varsity Football

From the days of playing against Ivy League college freshmen teams, Cheshire Academy has a rich history of success on the football field. Today, the Cats have established themselves as one of the top prep football programs in New England.


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. Under head coach Dave Dykeman, Cheshire Academy has produced 77 college football players in the last seven years. Those players have gone on to play at Alabama, Harvard, high-academic Division III institutions and others colleges.


The Cats play a highly competitive schedule which includes other regional powers such as Choate, The Hun School of Princeton and Deerfield Academy. The Cats play home games at 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.


A strong commitment to success has propelled the Cats to two Colonial League titles, and four New England Bowl championships in recent years.

Varsity Football Schedule



  • Win


  • Loss


  • Tie


  • %


Football Varsity Boys vs Hun School of Princeton – Home

1:00 pm

7 - 44 L

Football Varsity Boys vs Worcester Academy – Away

1:00 pm

35 - 7 W

Football Varsity Boys vs Capital Harbor Prep – Away

3:30 pm

21 - 6 W

Football Varsity Boys vs Brunswick – away

6:30 pm

0 - 19 L

Football Varsity Boys vs Suffield Academy – home

6:30 pm

17 - 35 L

Football Varsity Boys vs Choate – home

4:00 pm

21 - 25 L

Football Varsity Boys vs Wyoming Seminary – home

2:00 pm

42 - 0 W

Football Varsity Boys vs Deerfield Academy – home

4:00 pm

7 - 27 L

Football Varsity Boys vs St. Thomas More – away

1:00 pm

6 - 28 L