| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/8 | 7:00 p.m. | Varsity | League | Normal | Away | Watertown | Loss | 16-37 | | John J. Mills Complex @ Watertown High School | |
| THU 9/14 | 6:00 p.m. | Varsity | League | Normal | Home | SacredHeart | Win | 40-12 | | OHS Wolverine Field (Turf) | |
| FRI 9/22 | 7:00 p.m. | Varsity | League | Normal | Away | Ansonia | Loss | 0-43 | | Nolan Field, Ansonia | |
| FRI 9/29 | 6:00 p.m. | Varsity | League | Normal | Home | Crosby | Loss | 40-50 | | OHS Wolverine Field (Turf) | |
| FRI 10/6 | 6:30 p.m. | Varsity | League | Normal | Away | Woodland | Win | 42-14 | | Woodland Football Field | |
| FRI 10/20 | 6:00 p.m. | Varsity | League | Normal | Home | Derby | Loss | 26-32 | | OHS Wolverine Field (Turf) | |
| FRI 10/27 | 6:30 p.m. | Varsity | League | Normal | Away | Wolcott | Loss | 34-58 | | Wolcott High School, Monroe Field | |
| FRI 11/3 | 6:00 p.m. | Varsity | League | Normal | Home | Wilby | Win | 43-0 | | OHS Wolverine Field (Turf) | |
| FRI 11/10 | 6:00 p.m. | Varsity | League | Normal | Home | Seymour | Loss | 19-38 | | OHS Wolverine Field (Turf) | |
| WED 11/22 | 6:00 p.m. | Varsity | League | Normal | Away | StPaulCatholic | Loss | 22-44 | | St. Paul Catholic H.S. | |