| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:15 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Scofield Magnet Middle School - Cross Country Course | |
| Stamford | | |
| Westhill | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow - XC Course | |
| Staples | | |
| St. Joseph | | |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Away | Trumbull | | | | Trumbull High School - Cross Country Course | |
| Brien McMahon | | |
| Fairfield Ludlowe | | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Away | Darien | | | | Greenwich Point - Greenwich Point | |
| Danbury | | |
| Greenwich | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | | | | Waveny Park - Waveny Park | |
| Norwalk | | |
| Ridgefield | | |
| WED 10/16 | 2:30 PM | Varsity | Postseason | Normal | Away | Ridgefield | | | | Waveny Park - Waveny Park | |
| Norwalk | | |
| New Canaan | | |
| Greenwich | | |
| Danbury | | |
| Darien | | |
| Brien McMahon | | |
| Fairfield Ludlowe | | |
| Fairfield Warde | | |
| Trumbull | | |
| Westhill | | |
| Staples | | |
| St. Joseph | | |
| Stamford | | |
| Wilton | | |