| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/9 | 7:00 p.m. | Varsity | League | Normal | Away | JosephForan | Loss | 41-43 | | Foran High School -Foran High School - Turf Field | |
| FRI 9/16 | 7:00 p.m. | Varsity | League | Normal | Home | Bunnell | Loss | 20-45 | | Weston High School-WHS Stadium Field | |
| SAT 9/24 | 12:00 p.m. | Varsity | League | Normal | Away | LewisMills | Win | 42-7 | | Lewis Mills High School-Lewis Mills Track | |
| FRI 9/30 | 7:00 p.m. | Varsity | League | Normal | Away | Stratford | Loss | 24-26 | | Penders Field-Penders Field - Stratford | |
| FRI 10/14 | 7:00 p.m. | Varsity | League | Normal | Away | NewFairfield | Loss | 20-26 | | New Fairfield High School-Stadium Field | |
| FRI 10/21 | 7:00 p.m. | Varsity | League | Normal | Home | Bethel | Win | 50-13 | | Weston High School-WHS Stadium Field | |
| FRI 10/28 | 7:00 p.m. | Varsity | League | Normal | Home | Masuk | Loss | 13-45 | | Weston High School-WHS Stadium Field | |
| FRI 11/4 | 7:00 p.m. | Varsity | League | Normal | Home | Brookfield | Win | 34-14 | | Weston High School-WHS Stadium Field | |
| MON 11/14 | 6:30 p.m. | Varsity | League | Normal | Away | NotreDameCatholic | Win | 3-0 | | Sacred Heart University-Campus Field | |
| WED 11/23 | 4:30 p.m. | Varsity | League | Normal | Home | JoelBarlow | Loss | 20-56 | | Weston High School-WHS Stadium Field | |