| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Pomperaug | | | | Pomperaug High School - Cross Country Course | 2:15 PM - 1 Bus - STA |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Bridgeport Central | | | | Tarrywile Park - Tarrywile Park | |
| Brien McMahon | | |
| New Canaan | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | | | | Staples High School - Staples Stadium | 2:00 PM - 1 Bus - STA |
| Fairfield Warde | | |
| Staples | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | Darien | | | | Tarrywile Park - Tarrywile Park | |
| Fairfield Ludlowe | | |
| Stamford | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Ridgefield | | | | Allen's Meadow - XC Course | 2:15 PM - 1 Bus - Elite Limousine 631636 Boys & Girls XC 56 passenger |
| Wilton | | |
| Westhill | | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | Greenwich | | | | Greenwich Point - Greenwich Point | 2:15 PM - 1 Bus - Coach America coach bus (1 bus Boys & Girls) |
| Norwalk | | |
| Trumbull | | |
| WED 10/18 | 2:15 PM | Varsity | Postseason | Normal | Away | Stamford | | | | Waveny Park - Waveny Park | 12:01 AM - 1 Bus - STA |
| Ridgefield | | |
| Brien McMahon | | |
| Fairfield Ludlowe | | |
| Darien | | |
| St. Joseph | | |
| Greenwich | | |
| Trumbull | | |
| | |
| Westhill | | |
| New Canaan | | |
| Norwalk | | |
| Wilton | | |
| Fairfield Warde | | |
| Bridgeport Central | | |
| Staples | | |