| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/13 | 7:00 p.m. | Varsity | League | Normal | Home | FitchSr | Win | 31-14 | | Wilton High School-Veterans Memorial Stadium | |
| FRI 9/20 | 7:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Win | 37-0 | | Wilton High School-Veterans Memorial Stadium | |
| FRI 9/27 | 7:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 14-56 | | Wilton High School-Veterans Memorial Stadium | |
| FRI 10/4 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Win | 42-6 | | Fairfield Warde HS-Tetreau/Davis Field | |
| FRI 10/18 | 5:30 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 0-21 | | Ridgefield High School-Tiger Hollow Stadium | |
| FRI 10/25 | 7:00 p.m. | Varsity | League | Normal | Away | Bunnell | Win | 45-14 | | Bunnell High School-Bunnell Turf Field | |
| FRI 11/1 | 7:00 p.m. | Varsity | League | Normal | Home | Staples | Win | 35-24 | | Wilton High School-Veterans Memorial Stadium | |
| SAT 11/9 | 2:00 p.m. | Varsity | League | Normal | Home | Stamford | Win | 42-0 | | Wilton High School-Veterans Memorial Stadium | |
| FRI 11/15 | 7:00 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 20-38 | | New Canaan High School-Dunning Stadium | |
| THU 11/28 | 10:00 a.m. | Varsity | League | Normal | Away | TrinityCatholic | Win | 63-20 | | Trinity Catholic-Gaglio Field | |