| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/13 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Scofield Magnet Middle School - Cross Country Course | 3:00 PM |
| Westhill | | |
| Norwalk | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | Ridgefield | | | | Trumbull High School - Cross Country Course | 2:15 PM |
| Bridgeport Central | | |
| Trumbull | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Danbury | | | | Tarrywile Park - Tarrywile Park | 2:15 PM |
| Darien | | |
| Fairfield Ludlowe | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | | | | Waveny Park - Waveny Park | 2:30 PM |
| Greenwich | | |
| St. Joseph | | |
| WED 10/11 | 4:00 PM | Varsity | League | Normal | Away | Brien McMahon | | | | Allen's Meadow - XC Course | 2:30 PM |
| Staples | | |
| Wilton | | |
| WED 10/18 | 2:15 PM | Varsity | Postseason | Normal | Away | New Canaan | | | | Waveny Park - Waveny Park | 12:30 PM |
| Norwalk | | |
| Westhill | | |
| Fairfield Ludlowe | | |
| St. Joseph | | |
| Danbury | | |
| Staples | | |
| Wilton | | |
| | |
| Fairfield Warde | | |
| Ridgefield | | |
| Greenwich | | |
| Trumbull | | |
| Darien | | |
| Bridgeport Central | | |
| Brien McMahon | | |