| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:15 PM | Varsity | League | Normal | Away | Bridgeport Central | | | | Scofield Magnet Middle School - Cross Country Course | |
| Stamford | | |
| Westhill | | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Away | Brien McMahon | | | | Waveny Park - Waveny Park | |
| New Canaan | | |
| Staples | | |
| MON 10/7 | 4:00 PM | Varsity | League | Normal | Away | Darien | | | | Fairfield Ludlowe High School - Taft Field | |
| Fairfield Ludlowe | | |
| Wilton | | |