| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Daniel Hand | | | | Sheehan High School - Sheehan HS Cross Country Course | 2:15 PM - 1 Bus |
| North Branford | | |
| Coginchaug | | |
| Jonathan Law | | |
| Foran | | |
| North Haven | | |
| Cromwell | | |
| Sheehan | | |
| FRI 9/15 | 3:45 PM | Varsity | League | Normal | Home | Career Magnet | | | | Wharton Brook State Park - Wharton Brook State Park | |
| Fairfield Prep | | |
| Jonathan Law | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | East Haven | | | | Carrigan Middle School - Cardigan ms | 2:15 PM - 1 Bus |
| Notre Dame-West Haven | | |
| Daniel Hand | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Prep | | | | Guilford High School - Guilford Fair grounds | |
| Xavier | | |
| Shelton | | |
| Guilford | | |
| Jonathan Law | | |
| Career Magnet | | |
| Hillhouse | | |
| Amity | | |
| Wilbur Cross | | |
| Cheshire | | |
| Notre Dame-West Haven | | |
| Branford | | |
| Hamden | | |
| Daniel Hand | | |
| North Haven | | |
| East Haven | | |
| Sheehan | | |
| Foran | | |
| West Haven | | |
| WED 10/4 | 3:45 PM | Varsity | League | Normal | Home | Sheehan | | | | Wharton Brook State Park - Wharton Brook State Park | |
| TUE 10/10 | 4:15 PM | Varsity | League | Normal | Away | Xavier | | | | Mercy High School - Cross Country Course | 2:15 PM - 1 Bus |
| Hillhouse | | |
| North Haven | | |
| FRI 10/13 | 4:30 PM | Varsity | League | Normal | Away | Cheshire | | | | Cheshire Park - Field 1 | 2:15 PM - 1 Bus |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Jonathan Law | | | | East Shore Athletic Complex - Trail | |
| Foran | | |
| Notre Dame-West Haven | | |
| Xavier | | |
| Fairfield Prep | | |
| West Haven | | |
| North Haven | | |
| Cheshire | | |
| Hillhouse | | |
| Amity | | |
| Hamden | | |
| Career Magnet | | |
| Wilbur Cross | | |
| Branford | | |
| Sheehan | | |
| Daniel Hand | | |
| Shelton | | |
| East Haven | | |
| Guilford | | |