| 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 | EastLyme | Win | 45-0 | | Madison Surf Club-Turf Field | |
| FRI 9/16 | 7:00 p.m. | Varsity | League | Normal | Away | Shelton | Loss | 0-28 | | Shelton High School-Finn Stadium | |
| FRI 9/23 | 7:00 p.m. | Varsity | League | Normal | Home | Newtown | Loss | 0-28 | | Madison Surf Club-Turf Field | |
| FRI 9/30 | 7:00 p.m. | Varsity | League | Normal | Away | Cheshire | Loss | 0-28 | | Cheshire High Main Game field | |
| FRI 10/14 | 7:00 p.m. | Varsity | League | Normal | Home | NotreDame | Loss | 7-34 | | Madison Surf Club-Turf Field | |
| FRI 10/21 | 7:00 p.m. | Varsity | League | Normal | Home | FairfieldCollegePreparatory | Loss | 19-37 | | Madison Surf Club-Turf Field | |
| FRI 10/28 | 7:00 p.m. | Varsity | League | Normal | Away | Xavier | Win | 21-7 | | Xavier High School-Larry McHugh Field | |
| FRI 11/4 | 7:00 p.m. | Varsity | League | Normal | Away | NorthHaven | Loss | 14-35 | | North Haven Middle School-East Turf Field | |
| SAT 11/12 | 6:00 p.m. | Varsity | League | Normal | Home | Sheehan | Loss | 13-17 | | Madison Surf Club-Turf Field | |
| WED 11/23 | 7:00 p.m. | Varsity | League | Normal | Away | Guilford | Win | 28-25 | | Guilford High School-Kavanaugh Turf Field and Track | |