| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SUN 9/15 | 3:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 21-24 | | Lyman Hall Fitzgerald Field | |
| FRI 9/20 | 7:00 p.m. | Varsity | League | Normal | Away | Cheshire | Loss | 7-47 | | Cheshire High Main Game field | |
| FRI 9/27 | 7:00 p.m. | Varsity | League | Normal | Away | Guilford | Loss | 0-44 | | Kavanaugh Turf Field at GHS | |
| FRI 10/4 | 7:00 p.m. | Varsity | League | Normal | Home | AmityReg | Loss | 19-49 | | Lyman Hall Fitzgerald Field | |
| THU 10/10 | 3:30 p.m. | Varsity | League | Normal | Away | JamesHillhouse | Loss | 20-54 | | Wilbur Cross Athletic Complex | |
| FRI 10/18 | 7:00 p.m. | Varsity | League | Normal | Home | JosephForan | Loss | 18-54 | | Lyman Hall Fitzgerald Field | |
| FRI 10/25 | 7:00 p.m. | Varsity | League | Normal | Away | EastHaven | Win | 22-14 | | East Haven High School | |
| FRI 11/1 | 7:00 p.m. | Varsity | League | Normal | Home | Branford | Win | 24-21 (OT) | | Lyman Hall Fitzgerald Field | |
| FRI 11/8 | 7:00 p.m. | Varsity | League | Normal | Home | HydeLeadership | Loss | 14-19 | | Lyman Hall Fitzgerald Field | |
| FRI 11/15 | 7:00 p.m. | Varsity | League | Normal | Home | JonathanLaw | Loss | 14-40 | | Lyman Hall Fitzgerald Field | |
| THU 11/28 | 10:00 a.m. | Varsity | League | Normal | Away | Sheehan | Loss | 7-54 | | Sheehan HS Riccitelli Field | |