| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Lyman Hall | | | | Falcon Field (Meriden, CT) - Football Field | 6:45 AM - 2 Buses |
| Platt | | |
| Woodland | | |
| THU 9/5 | 6:00 PM | Varsity | Scrimmage | Normal | Home | Lyman Hall | | | | Jonathan Law High School - Lawmen Stadium | |
| FRI 9/13 | 7:00 PM | Varsity | League | Normal | Home | Brookfield | | | | Jonathan Law High School - Lawmen Stadium | |
| FRI 9/20 | 7:00 PM | Varsity | League | Normal | Home | Notre Dame-West Haven | | | | Jonathan Law High School - Lawmen Stadium | |
| SAT 9/28 | 12:00 PM | Varsity | Non-League | Normal | Away | RHAM | | | | RHAM High School - Varsity Field | 9:00 AM - 2 Buses |
| FRI 10/4 | 7:00 PM | Varsity | League | Normal | Away | East Haven | | | | East Haven High School - EHHS Turf Field & Track | 4:30 PM - 2 Buses |
| THU 10/10 | 7:00 PM | Varsity | League | Normal | Home | Amity | | | | Jonathan Law High School - Lawmen Stadium | |
| FRI 10/25 | 6:00 PM | Varsity | League | Normal | Away | Hamden | | | | Hamden High School - HHS Turf #1 | 4:00 PM - 2 Buses |
| FRI 11/1 | 7:00 PM | Varsity | Non-League | Normal | Away | New Fairfield | | | | New Fairfield High School - Stadium Field | 3:45 PM - 2 Buses |
| FRI 11/8 | 6:30 PM | Varsity | League | Normal | Away | Sheehan | | | | Sheehan High School - Sheehan HS Riccitelli Field (Turf) | 4:00 PM - 2 Buses |
| FRI 11/15 | 7:00 PM | Varsity | League | Normal | Home | Shelton | | | | Jonathan Law High School - Lawmen Stadium | |
| THU 11/28 | 10:30 AM | Varsity | League | Normal | Home | Foran | | | | Jonathan Law High School - Lawmen Stadium | |