| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Wilton | | | | Trumbull High School - Cross Country Course | |
| St. Joseph | | |
| Darien | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Ridgefield | | | | Trumbull High School - Cross Country Course | |
| Stamford | | |
| Bridgeport Central | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Westhill | | | | Waveny Park - Waveny Park | 2:15 PM - 1 Bus |
| New Canaan | | |
| Staples | | |
| MON 10/2 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Hoyden's Hill Open Space - Cross Country Course | 2:45 PM - 1 Bus |
| Brien McMahon | | |
| Fairfield Ludlowe | | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | Greenwich | | | | Greenwich Point - Greenwich Point | 2:00 PM - 1 Bus |
| Norwalk | | |
| Danbury | | |
| WED 10/18 | 2:15 PM | Varsity | Postseason | Normal | Away | Stamford | | | | Waveny Park - Waveny Park | 11:30 AM - 1 Bus |
| Norwalk | | |
| Ridgefield | | |
| Danbury | | |
| Brien McMahon | | |
| Fairfield Ludlowe | | |
| Greenwich | | |
| Fairfield Warde | | |
| Darien | | |
| St. Joseph | | |
| Wilton | | |
| Westhill | | |
| Staples | | |
| | |
| New Canaan | | |
| Bridgeport Central | | |