| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Away | St. Paul Catholic | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Woodland | | |
| Watertown | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Home | WCA | | | | Holy Cross - Alumni Field | |
| Seymour | | |
| Wilby | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | East Hampton | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| Parish Hill | | |
| Platt | | |
| Avon | | |
| East Catholic | | |
| Coginchaug | | |
| Thomaston | | |
| Maloney | | |
| New London | | |
| Valley Regional | | |
| Old Saybrook | | |
| Nonnewaug | | |
| Hale Ray | | |
| Housatonic Regional | | |
| Portland | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Wolcott | | | | Wolcott High School - Front of Wolcott High School | |
| Naugatuck | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Torrington | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Oxford | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Derby | | | | Holy Cross - Alumni Field | |
| Kennedy | | |
| Crosby | | |