| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/4 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Glastonbury | | | | JB Williams Park - JB Williams Park | |
| Hale Ray | | |
| RHAM | | |
| FRI 9/6 | 3:30 PM | Varsity | Non-League | Normal | Away | | | | | Veterans Park | |
| TUE 9/10 | 4:00 PM | Varsity | Non-League | Normal | Home | East Hampton | | | | Camp Ingersoll - Camp Ingersoll | |
| Hale Ray | | |
| Plainville | | |
| FRI 9/13 | 3:30 PM | Varsity | Non-League | Normal | Away | South Windsor | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| University | | |
| Windham Tech | | |
| Windsor | | |
| East Catholic | | |
| Northwest Catholic | | |
| Norwich Tech | | |
| Hartford Public | | |
| Ellis Tech | | |
| Lyman Memorial | | |
| East Hartford | | |
| East Windsor | | |
| Enfield | | |
| Bristol Central | | |
| Bristol Eastern | | |
| THU 9/19 | 4:00 PM | Varsity | Non-League | Normal | Away | | | | | Not Listed | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Coginchaug | | | | Camp Ingersoll - Camp Ingersoll | |
| Old Lyme | | |
| Westbrook | | |
| Old Saybrook | | |
| Hale Ray | | |
| SAT 9/28 | 10:00 AM | Varsity | Non-League | Normal | Away | | | | | Not Listed | |
| FRI 10/4 | 10:00 AM | Varsity | Non-League | Normal | Away | | | | | Not Listed - Thetford, VT | |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | | | | | Hammonasset Park | |
| | |
| Coginchaug | | |
| Coginchaug | | |
| Cromwell | | |
| Cromwell | | |
| Haddam Killingworth | | |
| Haddam Killingworth | | |
| East Hampton | | |
| East Hampton | | |
| East Hampton | | |
| East Hampton | | |
| Old Lyme | | |
| Old Lyme | | |
| Morgan | | |
| Morgan | | |
| Old Saybrook | | |
| Old Saybrook | | |
| Old Saybrook | | |
| Old Saybrook | | |
| Hale Ray | | |
| Hale Ray | | |
| North Branford | | |
| North Branford | | |
| Valley Regional | | |
| Valley Regional | | |
| Westbrook | | |
| Westbrook | | |