| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/13 | 4:00 p.m. | Varsity | League | Normal | Away | Trumbull | | | | Trumbull High School-Cross Country Course | |
| TUE 9/20 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | | | | Scofield Magnet Middle School-Cross Country Course | |
| WED 9/28 | 4:30 p.m. | Varsity | League | Normal | Away | NewCanaan | | | | Waveny Park | |
| MON 10/3 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | | | | Staples High School-Staples Stadium | |
| WED 10/12 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | | | | Fairfield Ludlowe High School-Taft Field | |