| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/13 | 6:30 p.m. | Varsity | League | Normal | Home | Bethel | Win | 34-7 | | Pomperaug High School-Stadium | |
| FRI 9/20 | 6:30 p.m. | Varsity | League | Normal | Home | Farmington | Loss | 21-28 | | Pomperaug High School-Stadium | |
| SAT 9/28 | 11:00 a.m. | Varsity | League | Normal | Away | BristolEastern | Loss | 0-14 | | Bristol Eastern High School-Alumni Field-Turf | |
| FRI 10/4 | 6:30 p.m. | Varsity | League | Normal | Home | Newtown | Loss | 0-35 | | Pomperaug High School-Stadium | |
| FRI 10/18 | 7:00 p.m. | Varsity | League | Normal | Away | Hamden | Loss | 7-28 | | Hamden High School-HHS Turf Field #1 | |
| FRI 10/25 | 6:30 p.m. | Varsity | League | Normal | Home | NorthHaven | Loss | 0-41 | | Pomperaug High School-Stadium | |
| FRI 11/1 | 7:00 p.m. | Varsity | League | Normal | Away | Bunnell | Loss | 13-18 | | Bunnell High School-Bunnell Turf Field | |
| FRI 11/8 | 7:00 p.m. | Varsity | League | Normal | Home | Masuk | Loss | 0-51 | | Pomperaug High School-Stadium | |
| FRI 11/15 | 7:00 p.m. | Varsity | League | Normal | Away | NewMilford | Loss | 6-12 | | New Milford High School-Joe Wiser Stadium - NMHS | |
| THU 11/28 | 10:00 a.m. | Varsity | League | Normal | Away | NotreDameCatholic | Win | 47-33 | | Notre Dame - Fairfield-McCarty Stadium | |