| 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 | 3:30 PM |
| Fairfield Warde | | |
| Westhill | | |
| SAT 9/14 | 10:00 AM | Varsity | League | Normal | Away | | | | | Not Listed - Wilton High School | 8:00 AM |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Danbury | | | | Waveny Park - Waveny Park | 2:30 PM |
| Fairfield Ludlowe | | |
| New Canaan | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Away | Darien | | | | Staples High School - Staples Stadium | 2:30 PM |
| Ridgefield | | |
| Staples | | |
| SAT 9/28 | 12:01 AM | Varsity | League | Normal | Away | | | | | Not Listed - Wickham Park | 7:30 AM |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Norwalk | | | | Allen's Meadow - XC Course | 2:30 PM |
| Trumbull | | |
| Wilton | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | St. Joseph | | | | St. Joseph High School - Trail | 2:30 PM |
| Greenwich | | |
| Brien McMahon | | |
| WED 10/16 | 2:30 PM | Varsity | Postseason | Normal | Away | Brien McMahon | | | | Waveny Park - Waveny Park | |
| Bridgeport Central | | |
| Darien | | |
| Fairfield Ludlowe | | |
| Danbury | | |
| New Canaan | | |
| Norwalk | | |
| Fairfield Warde | | |
| Greenwich | | |
| Trumbull | | |
| Westhill | | |
| Wilton | | |
| St. Joseph | | |
| Ridgefield | | |
| Staples | | |