| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 4:30 p.m. | Varsity | League | Normal | Away | NewCanaan | | | | Waveny Park | |
| WED 9/22 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | | | | Tarrywile Park | |
| SAT 9/25 | 12:00 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Winding Trails-Cross Country Course | |
| WED 9/29 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | | | | Staples High School-Staples Stadium | |
| TUE 10/5 | 4:00 p.m. | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow-XC Course | |
| SAT 10/9 | 9:00 a.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Wickham Park | |
| TUE 10/12 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | | | | Fairfield Ludlowe High School-Taft Field | |