| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Brien McMahon | Loss | 40-69 | | Ridgefield High School - Upper Grass Field | |
| Danbury | Loss | 40-22 |
| Ridgefield | Loss | 40-115 |
| SAT 9/14 | 9:00 AM | Varsity | League | Normal | Home | Greenwich | | | | Allen's Meadow - XC Course | |
| Staples | | |
| | |
| SAT 9/14 | 9:00 AM | Varsity | Non-League | Normal | Home | Guilford | | | | Allen's Meadow - XC Course | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | Bridgeport Central | | | | Allen's Meadow - XC Course | |
| Staples | | |
| St. Joseph | | |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Away | Westhill | | | | Greenwich Point - Greenwich Point | 2:30 PM - 1 Bus |
| Greenwich | | |
| New Canaan | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Home | Norwalk | | | | Allen's Meadow - XC Course | |
| Stamford | | |
| Trumbull | | |
| MON 10/7 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | | | | Fairfield Ludlowe High School - Taft Field | |
| Fairfield Warde | | |
| Darien | | |
| WED 10/16 | 2:30 PM | Varsity | Postseason | Normal | Away | Darien | | | | Waveny Park - Waveny Park | |
| Fairfield Ludlowe | | |
| Danbury | | |
| Bridgeport Central | | |
| Brien McMahon | | |
| Greenwich | | |
| Fairfield Warde | | |
| New Canaan | | |
| Norwalk | | |
| Trumbull | | |
| Westhill | | |
| Ridgefield | | |
| Stamford | | |
| Staples | | |
| St. Joseph | | |