| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 4:00 p.m. | Varsity | League | Normal | Away | Greenwich | | | | Greenwich Point | |
| TUE 10/6 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | | | | Waveny Park | |
| TUE 10/13 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | | | | Scofield Magnet Middle School-Cross Country Course | |
| TUE 10/20 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | | | | Darien High School-DHS Stadium East | |
| TUE 10/27 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | | | | Scofield Magnet Middle School-Cross Country Course | |