| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Jonathan Law | | | | Falcon Field (Meriden, CT) - Football Field | 7:45 AM - 1 Bus |
| Platt | | |
| Woodland | | |
| THU 9/5 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Jonathan Law | | | | Jonathan Law High School - Lawmen Stadium | 4:00 PM - 3 Buses |
| FRI 9/13 | 6:30 PM | Varsity | League | Normal | Home | East Haven | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 9/20 | 7:00 PM | Varsity | League | Normal | Away | Branford | | | | Branford High School - Athletic Turf Field | 5:00 PM - 3 Buses |
| FRI 9/27 | 7:00 PM | Varsity | League | Normal | Away | Amity | | | | Amity Regional High School - William Johnson Stadium Field | 4:45 PM - 3 Buses |
| FRI 10/4 | 6:30 PM | Varsity | League | Normal | Home | Hillhouse | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 10/11 | 6:00 PM | Varsity | Non-League | Normal | Away | New London | | | | New London High School - Pat Cannamela Field | 3:15 PM - 3 Buses |
| FRI 10/25 | 6:30 PM | Varsity | League | Normal | Home | Wilbur Cross | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 11/1 | 6:30 PM | Varsity | League | Normal | Home | Guilford | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 11/8 | 6:30 PM | Varsity | League | Normal | Home | Harding | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 11/15 | 6:00 PM | Varsity | League | Normal | Away | Bassick | | | | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) | 3:45 PM - 3 Buses |
| THU 11/28 | 10:00 AM | Varsity | League | Normal | Away | Sheehan | | | | Sheehan High School - Sheehan HS Riccitelli Field (Turf) | 8:30 AM - 3 Buses |