| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 3:45 PM | Varsity | Scrimmage | Normal | Home | Berlin | | | | Cromwell High School - cross country course | |
| Granby Memorial | | |
| Hale Ray | | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Coginchaug | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Daniel Hand | | |
| Jonathan Law | | |
| Foran | | |
| Lyman Hall | | |
| North Branford | | |
| North Haven | | |
| Sheehan | | |
| WED 9/27 | 3:30 PM | Varsity | League | Normal | Away | East Hampton | | | | John Winthrop Middle School - John Winthrop Middle School | |
| Haddam Killingworth | | |
| Morgan | | |
| North Branford | | |
| Valley Regional | | |
| FRI 10/13 | 4:00 PM | Varsity | Non-League | Normal | Away | Bulkeley | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| East Catholic | | |
| East Hartford | | |
| Enfield | | |
| Ellis Tech | | |
| Lyman Memorial | | |
| Hale Ray | | |
| Norwich Tech | | |
| Parish Hill | | |
| RHAM | | |
| South Windsor | | |
| University | | |
| Windham | | |
| Windsor | | |
| Hall | | |