| 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 | |
| ATI | | |
| Lewis Mills | | |
| Masuk | | |
| New Fairfield | | |
| Seymour | | |
| Weston | | |
| FRI 9/1 | 5:15 PM | Varsity | Scrimmage | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Field I (Stadium) | 12:00 PM |
| FRI 9/8 | 7:00 PM | Varsity | League | Normal | Home | East Haven | Win | 48-14 | | Warren Harding High School - Lewis Field | |
| FRI 9/15 | 7:00 PM | Varsity | League | Normal | Away | Xavier | Loss | 8-49 | | Xavier High School - Larry McHugh Field | |
| FRI 9/22 | 6:30 PM | Varsity | Non-League | Normal | Away | Pomperaug | Loss | 8-41 | | Pomperaug High School - Stadium | |
| FRI 10/6 | 7:00 PM | Varsity | League | Normal | Home | Lyman Hall | Loss | 16-27 | | Warren Harding High School - Lewis Field | |
| FRI 10/13 | 7:00 PM | Varsity | League | Normal | Away | Guilford | Loss | 6-56 | | Guilford High School - Kavanaugh Turf Field and Track | |
| FRI 10/20 | 6:00 PM | Varsity | League | Normal | Away | Hillhouse | Win | 12-6 | | Bowen Field - Football Field | |
| FRI 10/27 | 7:00 PM | Varsity | Non-League | Normal | Home | Norwich Free Academy | Loss | 22-30 | | Warren Harding High School - Lewis Field | |
| THU 11/9 | 6:00 PM | Varsity | League | Normal | Home | Bassick | Win | 48-13 | | Warren Harding High School - Lewis Field | |
| THU 11/16 | 7:00 PM | Varsity | League | Normal | Away | Foran | Loss | 20-50 | | Foran High School - Foran High School - Turf Field | |
| THU 11/23 | 10:00 AM | Varsity | Non-League | Normal | Home | Bridgeport Central | Win | 48-14 | | Warren Harding High School - Lewis Field | |