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.

November 9

vs st. thomas more

01:00 pm


St. Thomas More School

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November 2

vs deerfield academy

04:00 pm


CA Simosa Field

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October 26

vs wyoming seminary

02:00 pm


CA Simosa Field

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October 19

vs choate

04:00 pm


CA Simosa Field

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October 4

vs suffield academy

06:30 pm


Suffield Academy

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September 27

vs brunswick

06:30 pm


Brunswick School

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September 21

vs capital harbor prep

03:30 pm


Capital Prep Harbor

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September 14

vs worcester academy

01:00 pm


Worcester Academy

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September 7

vs hun school of princeton

01:00 pm


Hun School of Princeton

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Football Varsity Boys vs St. Thomas More – away

Cheshire Academy fell 28-6 to St. Thomas More in its season finale on Saturday at Oakdale, Connecticut. 

Cole Baker ’21 kicked a pair of field goals (38, 32 yards) for the Cats. 

Cheshire 6 - 28 Opponent

Football Varsity Boys vs Deerfield Academy – home

Cheshire Academy’s defense forced three turnovers in a 27-7 loss to Deerfield Academy on Saturday at Simosa Field. 

Jackson Parker ’20 caught three passes for 85 yards, including a 63-yard touchdown pass from Jack Brandon ’21. Parker also recorded an interception. 

The Cats honored its senior class during a pregame ceremony. 

Cheshire 7 - 27 Opponent

Football Varsity Boys vs Wyoming Seminary – home

Cheshire Academy rolled to a 42-0 win over Wyoming Seminary on Saturday at Simosa Field. 

JT Perry ’20 returned an interception 30 yards for a touchdown in the opening quarter to highlight a stellar defensive effort for the Cats. Jack Brandon ’20 and the Cheshire Academy offense took care of the rest.

Brandon completed 7-of-14 passes for 171 yards and two touchdowns. Jackson Parker ’20 caught three passes for 103 yards, including a 75-yard touchdown early in the first.  Jack Roberge ’20 had five rushes for 50 yards and a touchdown, and also recorded an interception.

Nick Resendiz ’20 caught a 10-yard touchdown from Brandon and Jace Lopez ’21 had a 3-yard touchdown run. 

The Cats led 21-0 at half. 



Cheshire 42 - 0 Opponent

Football Varsity Boys vs Choate – home

The Cheshire Academy football team fell 25-21 to Choate in front of a packed house at Simosa Field to cap Homecoming & Family Weekend on Saturday. 

The Cats held a 21-19 lead in the final minutes before Choate scored the go-ahead touchdown. 

Jack Brandon ’21 threw for 160 yards and two touchdowns. Jordan Robinson ’20 caught three passes for 75 yards and a touchdown, and Jackson Parker ’20 hauled in two passes for 65 yards and a score. Jack Roberge added a touchdown in the third on a 4-yard run. 

Cody Keith ’11 was inducted into the Kevin Slaughter Memorial Athletic Hall of Fame during a pregame ceremony. 

Cheshire 21 - 25 Opponent

Football Varsity Boys vs Suffield Academy – home

Cheshire Academy fell 35-17 to Suffield Academy on Friday night at Suffield. 

Ryan Stefanik ’20 caught a 4-yard touchdown pass in the third quarter from Jack Roberge ’20 and Nick Resendiz ’20 ran for a 12-yard score in the fourth for the Cats. Cheshire Academy got off to a slow start and trailed 21-3 at half. 

Cole Baker ’22 kicked a 35-yard field goal shortly before halftime. 

Cheshire 17 - 35 Opponent

Football Varsity Boys vs Brunswick – away

Jackson Parker ’20 caught seven passes for 85 yards in Cheshire Academy’s 17-0 loss to Brunswick on Friday night at Greenwich. 

Jordan Robinson ’20 added four catches for 60 yards. The Cats trailed 7-0 at half and lost a fumble inside Brunswick’s 5-yard line right before half.

Cheshire 0 - 19 Opponent

Football Varsity Boys vs Capital Harbor Prep – Away

Wilfredo Aybar ’22 highlighted a strong defensive effort, as Cheshire Academy knocked off Capital Harbor Prep 21-6 on Saturday at Bridgeport. 

Jack Brandon ’21 connected with Cam Maddox ’20 for a 22-yard touchdown pass in the first quarter and Capital Harbor answered back in the second. 

But Cheshire Academy’s defense halted the Sharks’ attack after that and scored 14 unanswered points in the second half. 

Brandon found Jackson Parker ’20 for a 30-yard touchdown in the third and then hit Charlie Davis ’20 for a 27-yard score in the fourth.

Brandon finished with 210 yards and three touchdowns on 17-of-22 passing. Parker caught five passes for 70 yards and a score, and Jack Roberge ’20 had 15 carries for 50 yards.

Cheshire 21 - 6 Opponent

Football Varsity Boys vs Worcester Academy – Away

Jack Brandon ’21 scored four touchdowns to lead the Cats to a 35-7 win on the road at Worcester Academy on Saturday. 

Cam Maddox ’20 scored on a 10-yard run in the opening quarter to put the Cats up 7-0. Worcester Academy responded with a touchdown, but Cheshire Academy went on to score 28 unanswered points and cruise to its first win. 

Bradon scored on a 2-yard run and then connected on a 7-yard touchdown pass to Wilfredo Aybar ’22 in the second quarter. Brandon then followed with a 15-yard touchdown pass to Jackson Parker in the third and the tandem connected again in the fourth on an 80-yard score. 

Cheshire 35 - 7 Opponent

Football Varsity Boys vs Hun School of Princeton – Home

Cheshire Academy fell 44-7 to The Hun School  (NJ) in its season opener on Saturday at Simosa Field in Cheshire. 

Hun, expected to be one of the strongest teams the Cats will face this season, scored on its opening drive. Cheshire Academy responded with a touchdown, as Jack Brandon ’21 connected with Jackson Parker ’20 on a 50-yard score. Hun went on to score 38 unanswered points. 

Jack Roberge ’20 finished with 15 carries for 60 yards for the Cats. 

Cheshire 7 - 44 Opponent


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