| 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 | WestHaven | Loss | 0-42 | | HHS Turf Field #1 | |
| FRI 9/16 | 7:00 p.m. | Varsity | League | Normal | Home | NorthHaven | Loss | 0-54 | | HHS Turf Field #1 | |
| FRI 9/23 | 7:00 p.m. | Varsity | League | Normal | Away | LymanHall | Win | 26-13 | | Lyman Hall Fitzgerald Field | |
| FRI 9/30 | 7:00 p.m. | Varsity | League | Normal | Away | JosephForan | Loss | 8-22 | | Foran High School - Turf Field | |
| FRI 10/7 | 6:00 p.m. | Varsity | League | Normal | Away | FairfieldCollegePreparatory | Loss | 6-28 | | Rafferty Stadium, Fairfield University | |
| FRI 10/21 | 7:00 p.m. | Varsity | League | Normal | Away | EastHaven | Win | 30-24 | | East Haven High School | |
| FRI 10/28 | 7:00 p.m. | Varsity | League | Normal | Home | JamesHillhouse | Loss | 8-41 | | HHS Turf Field #1 | |
| FRI 11/4 | 7:00 p.m. | Varsity | League | Normal | Away | AmityReg | Loss | 20-40 | | William Johnson Football Field @ Amity HS | |
| FRI 11/11 | 7:00 p.m. | Varsity | League | Normal | Home | WilburCross | Loss | 8-26 | | HHS Turf Field #1 | |
| THU 11/24 | 10:30 a.m. | Varsity | League | Normal | Home | NotreDame | Loss | 6-55 | | HHS Turf Field #1 | |