| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 p.m. | Varsity | League | Normal | Away | Glastonbury | | | | JB Williams Park | |
| TUE 9/17 | 3:45 p.m. | Varsity | League | Normal | Home | NorthwestCatholic | | | | Winding Trails-Cross Country Course | |
| SAT 9/21 | 3:45 p.m. | Varsity | League | Normal | Home | Middletown | | | | Winding Trails-Cross Country Course | |
| SAT 9/21 | 12:00 p.m. | Varsity | League | Normal | Home | Enfield | | | | Winding Trails-Cross Country Course | |
| SAT 9/21 | TBA | Varsity | League | Normal | Home | Glastonbury | | | | Winding Trails-Cross Country Course | |
| TUE 9/24 | 3:45 p.m. | Varsity | League | Normal | Away | Conard | | | | Reservoir Rt. 4 | |
| TUE 10/8 | 3:45 p.m. | Varsity | League | Normal | Home | Avon | | | | Winding Trails-Cross Country Course | |