| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/14 | 9:00 AM | Varsity | League | Normal | Away | | | | | Allen's Meadow - XC Course | 7:00 AM - boys and girls going together |
| Greenwich | | |
| Wilton | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow - XC Course | 2:15 PM - BOYS AND GIRLS GOING TOGETHER - TOTAL BUSES 3 GOING / 2 RETURNING |
| St. Joseph | | |
| Bridgeport Central | | |
| SAT 9/28 | 9:00 AM | Varsity | League | Normal | Away | | | | | Wickham Park - Wickham Park | 6:30 AM - BOYS AND GIRLS GOING TOGETHER 3 BUSES |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Waveny Park - Waveny Park | 2:00 PM - BOYS AND GIRLS GOING TOGETHER |
| New Canaan | | |
| Brien McMahon | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Danbury | | | | Tarrywile Park - Tarrywile Park | 1:45 PM - GIRLS AND BOYS GOING TOGETHER - 3 BUSES |
| Trumbull | | |
| Westhill | | |
| WED 10/16 | 2:30 PM | Varsity | Postseason | Normal | Away | Wilton | | | | Waveny Park - Waveny Park | |
| Trumbull | | |
| Westhill | | |
| Danbury | | |
| Darien | | |
| Fairfield Ludlowe | | |
| Fairfield Warde | | |
| Bridgeport Central | | |
| Brien McMahon | | |
| New Canaan | | |
| Norwalk | | |
| Ridgefield | | |
| Stamford | | |
| St. Joseph | | |
| Greenwich | | |
| TUE 10/22 | 4:00 PM | Varsity | League | Normal | Away | | | | | Wilton High School - Allens Meadows Park | 2:15 PM - BOYS AND GIRLS GOING TOGETHER - 2 BUSES |
| THU 10/24 | 4:00 PM | Varsity | League | Normal | Away | | | | | Danbury High School - Tarrywile Park Course | 1:45 PM - GIRLS AND BOYS GOING TOGETHER 1 BUS |