| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/26 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Bethel | | | | Immaculate High School - Mustang Valley | |
| Harding | | |
| Masuk | | |
| Weston | | |
| ATI | | |
| Lewis Mills | | |
| Seymour | | |
| THU 8/31 | 6:00 PM | Varsity | Scrimmage | Normal | Home | Weaver | | | | New Fairfield High School - Stadium Field | |
| FRI 9/8 | Suspended | Varsity | Non-League | Suspended | Away | Windham | | | | Windham High School - Ferrigno Field | |
| SUN 9/10 | Suspended | Varsity | Non-League | Suspended | Away | Windham | | | | Windham High School - Ferrigno Field | |
| FRI 9/15 | 7:00 PM | Varsity | League | Normal | Home | Bunnell | Loss | 12-20 | | New Fairfield High School - Stadium Field | |
| FRI 9/22 | 7:00 PM | Varsity | Non-League | Normal | Home | Foran | Win | 48-13 | | New Fairfield High School - Stadium Field | |
| SUN 10/1 | 4:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | Loss | 6-28 | | Sacred Heart University - Campus Field | |
| FRI 10/13 | 7:00 PM | Varsity | League | Normal | Home | Newtown | Loss | 6-41 | | New Fairfield High School - Stadium Field | |
| FRI 10/20 | 6:30 PM | Varsity | League | Normal | Away | Brookfield | Loss | 6-28 | | Brookfield High School - BHS Stadium Field | |
| FRI 10/27 | 7:00 PM | Varsity | League | Normal | Away | Weston | Win | 33-7 | | Weston High School - WHS Stadium Field | |
| FRI 11/3 | 7:00 PM | Varsity | League | Normal | Home | Joel Barlow | Loss | 13-14 | | New Fairfield High School - Stadium Field | |
| FRI 11/10 | 7:00 PM | Varsity | League | Normal | Away | Bethel | Win | 42-7 | | Bethel High School - DeSantis Field at Bethel High | |
| THU 11/16 | 6:00 PM | Varsity | Non-League | Normal | Away | Windham | Win | 40-20 | | Windham High School - Ferrigno Field | |
| THU 11/23 | 10:00 AM | Varsity | League | Normal | Home | New Milford | Loss | 7-22 | | New Fairfield High School - Stadium Field | |