| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | | | | Scofield Magnet Middle School-Cross Country Course | |
| WED 9/22 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | | | | Tarrywile Park | |
| TUE 9/28 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | | | | Darien High School-DHS Stadium East | |
| TUE 10/5 | 4:00 p.m. | Varsity | League | Normal | Away | StJoseph | | | | St. Joseph High School-Trail | |
| TUE 10/12 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | | | | Waveny Park | |