| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 9/11 | Canceled | Varsity | League | Canceled | Home | Hillhouse | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| East Haven | | |
| West Haven | | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Home | Cromwell | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Daniel Hand | | |
| Jonathan Law | | |
| Lyman Hall | | |
| Foran | | |
| Coginchaug | | |
| North Branford | | |
| North Haven | | |
| MON 9/18 | 4:00 PM | Varsity | League | Normal | Away | Wilbur Cross | | | | East Rock Park - East Rock Park | 2:15 PM |
| Xavier | | |
| Jonathan Law | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Shelton | | | | Guilford High School - Guilford Fair grounds | |
| Fairfield Prep | | |
| West Haven | | |
| Amity | | |
| Foran | | |
| Wilbur Cross | | |
| Xavier | | |
| Jonathan Law | | |
| Daniel Hand | | |
| Hillhouse | | |
| Career Magnet | | |
| Hamden | | |
| Lyman Hall | | |
| Notre Dame-West Haven | | |
| Cheshire | | |
| North Haven | | |
| Guilford | | |
| Branford | | |
| East Haven | | |
| WED 10/4 | 3:45 PM | Varsity | League | Normal | Away | Lyman Hall | | | | Wharton Brook State Park - Wharton Brook State Park | 2:15 PM |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Hamden | | | | Hamden Middle School - Back Field | 2:15 PM |
| Career Magnet | | |
| Guilford | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Wilbur Cross | | | | East Shore Athletic Complex - Trail | |
| Shelton | | |
| Jonathan Law | | |
| Career Magnet | | |
| Fairfield Prep | | |
| Daniel Hand | | |
| Hamden | | |
| Lyman Hall | | |
| Hillhouse | | |
| Foran | | |
| Amity | | |
| Cheshire | | |
| Notre Dame-West Haven | | |
| Guilford | | |
| West Haven | | |
| East Haven | | |
| Branford | | |
| North Haven | | |
| Xavier | | |