On Friday, Sep 29, 2023, the Cheshire Varsity Boys Football team won their Fairfield University-Rafferty Stadium game against Fairfield Prep High School by a score of 14-0.
On Friday, Sep 22, 2023, the Cheshire Varsity Boys Football team won their Cheshire High Main Game field game against Glastonbury High School by a score of 27-0.
On Thursday, Sep 14, 2023, the Cheshire Varsity Boys Football team won their Cheshire High Main Game field game against Shelton High School by a score of 21-14.
On Friday, Sep 8, 2023, the Cheshire Varsity Boys Football team won their Ridgefield High School-Tiger Hollow Stadium game against Ridgefield High School by a score of 39-10.