| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/2 | 10:00 AM | Freshman | Scrimmage | Normal | Home | Daniel Hand | | | | North Haven Middle School - East Turf Field | |
| THU 9/7 | 7:00 PM | Freshman | Non-League | Normal | Home | Darien | | | | North Haven Middle School - Vanacore Field | |
| THU 9/21 | 4:00 PM | Freshman | League | Normal | Home | Sheehan | | | | North Haven Middle School - Vanacore Field | |
| THU 9/28 | 4:00 PM | Freshman | League | Normal | Away | Notre Dame-West Haven | | | | Veterans Memorial Park (West Haven, CT) - Field | 3:00 PM |
| THU 10/5 | 4:00 PM | Freshman | League | Normal | Away | Fairfield Prep | | | | Fairfield University - Rafferty Stadium | 3:00 PM |
| FRI 10/20 | Canceled | Freshman | League | Canceled | Home | West Haven | | | | North Haven Middle School - Vanacore Field | |
| THU 10/26 | 4:00 PM | Freshman | League | Normal | Home | Shelton | | | | North Haven Middle School - Vanacore Field | |
| THU 11/2 | 6:00 PM | Freshman | League | Normal | Away | Cheshire | | | | Cheshire High Main Game field - Cheshire High Main Game field | 5:00 PM |
| WED 11/15 | 4:00 PM | Freshman | League | Normal | Home | Hamden | | | | North Haven Middle School - Vanacore Field | |