| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Coginchaug | | | | Sheehan High School - Sheehan HS Cross Country Course | 2:20 PM |
| Cromwell | | |
| Foran | | |
| Daniel Hand | | |
| Lyman Hall | | |
| Jonathan Law | | |
| Sheehan | | |
| North Branford | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | Amity | | | | Guilford High School - East River Preserve | 2:20 PM |
| Fairfield Prep | | |
| Guilford | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Guilford | | | | Guilford High School - Guilford Fair grounds | 2:15 PM |
| Foran | | |
| Hamden | | |
| Daniel Hand | | |
| Notre Dame-West Haven | | |
| Cheshire | | |
| Fairfield Prep | | |
| East Haven | | |
| Lyman Hall | | |
| Amity | | |
| Career Magnet | | |
| Jonathan Law | | |
| Branford | | |
| Wilbur Cross | | |
| Xavier | | |
| Sheehan | | |
| West Haven | | |
| Hillhouse | | |
| Shelton | | |
| TUE 10/10 | 4:15 PM | Varsity | League | Normal | Away | Hillhouse | | | | Mercy High School - Cross Country Course | 2:20 PM |
| Xavier | | |
| Lyman Hall | | |
| FRI 10/13 | 4:00 PM | Varsity | League | Normal | Home | Daniel Hand | | | | Wharton Brook State Park - Wharton Brook State Park | |
| Hamden | | |
| Shelton | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Shelton | | | | East Shore Athletic Complex - Trail | 11:15 AM |
| Hillhouse | | |
| West Haven | | |
| Sheehan | | |
| Xavier | | |
| Wilbur Cross | | |
| Hamden | | |
| Foran | | |
| Guilford | | |
| Daniel Hand | | |
| Cheshire | | |
| Notre Dame-West Haven | | |
| Lyman Hall | | |
| East Haven | | |
| Fairfield Prep | | |
| Branford | | |
| Jonathan Law | | |
| Career Magnet | | |
| Amity | | |