| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/9 | 7:00 p.m. | Varsity | League | Normal | Home | NewMilford | Win | 35-7 | | Cheshire High Main Game field | |
| FRI 9/16 | 6:00 p.m. | Varsity | League | Normal | Away | JamesHillhouse | Win | 30-0 | | Bowen Field-Football Field | |
| FRI 9/23 | 6:30 p.m. | Varsity | League | Normal | Away | Conard | Win | 34-7 | | Conard High School-McKee Stadium | |
| FRI 9/30 | 7:00 p.m. | Varsity | League | Normal | Home | DanielHand | Win | 28-0 | | Cheshire High Main Game field | |
| FRI 10/14 | 6:00 p.m. | Varsity | League | Normal | Away | FairfieldCollegePreparatory | Loss | 10-33 | | Fairfield University-Rafferty Stadium | |
| FRI 10/21 | 7:00 p.m. | Varsity | League | Normal | Home | NotreDame | Win | 27-12 | | Cheshire High Main Game field | |
| FRI 10/28 | 7:00 p.m. | Varsity | League | Normal | Home | NorthHaven | Loss | 0-10 | | Cheshire High Main Game field | |
| FRI 11/4 | 7:00 p.m. | Varsity | League | Normal | Away | Shelton | Loss | 14-34 | | Shelton High School-Finn Stadium | |
| SAT 11/12 | 1:30 p.m. | Varsity | League | Normal | Away | Xavier | Win | 26-0 | | Xavier High School-Larry McHugh Field | |
| THU 11/24 | 10:00 a.m. | Varsity | League | Normal | Home | Southington | Loss | 14-21 | | Cheshire High Main Game field | |