| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Away | Darien | | | | Staples High School - Staples Stadium | |
| Staples | | |
| Stamford | | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Away | Westhill | | | | Scofield Magnet Middle School - Cross Country Course | |
| St. Joseph | | |
| Fairfield Ludlowe | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | | | | Waveny Park - Waveny Park | |
| Norwalk | | |
| Bridgeport Central | | |