| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/10 | 3:30 p.m. | Varsity | League | Normal | Away | Sheehan | | | | Sheehan High School-Sheehan HS Cross Country Course | |
| SAT 9/11 | 9:00 a.m. | Varsity | League | Normal | Home | Tournament Game - Opponent Not Known | | | | East Shore Athletic Complex-Trail | |
| TUE 9/14 | 5:30 p.m. | Varsity | League | Normal | Away | WilburCross | | | | East Rock Park | |
| TUE 9/21 | 4:00 p.m. | Varsity | League | Normal | Away | Branford | | | | Branford Supply Pond | |
| SAT 10/2 | TBA | Varsity | League | Normal | Away | Guilford | | | | Guilford High School-Guilford Fair grounds | |
| SAT 10/23 | 9:00 a.m. | Varsity | League | Normal | Home | Tournament Game - Opponent Not Known | | | | Bowen Field-Football Field | |