| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Branford | | | | Fitzgerald Field - Fitzgerald Field | |
| Amity | | |
| Mercy | | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | North Branford | | | | Sheehan High School - Sheehan HS Cross Country Course | 2:15 PM |
| North Haven | | |
| Jonathan Law | | |
| Lyman Hall | | |
| Sheehan | | |
| Coginchaug | | |
| Cromwell | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Career Magnet | | | | EISENHOWER PARK - EISENHOWER PARK | |
| Shelton | | |
| West Haven | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | West Haven | | | | Guilford High School - Guilford Fair grounds | 1:45 PM |
| Shelton | | |
| North Haven | | |
| Lyman Hall | | |
| Jonathan Law | | |
| East Haven | | |
| Mercy | | |
| Sacred Heart Academy | | |
| Career Magnet | | |
| Hamden | | |
| Guilford | | |
| Branford | | |
| Lauralton Hall | | |
| Sheehan | | |
| Amity | | |
| Hillhouse | | |
| Wilbur Cross | | |
| Cheshire | | |
| Daniel Hand | | |
| MON 10/2 | 3:45 PM | Varsity | Non-League | Normal | Away | Amity | | | | Eisenhower Park - Eisenhower Park | 2:30 PM |
| Wilbur Cross | | |
| Lauralton Hall | | |
| Branford | | |
| North Haven | | |
| North Branford | | |
| Jonathan Law | | |
| West Haven | | |
| Sacred Heart Academy | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Lauralton Hall | | | | Eisenhower Park - Eisenhower Park | 2:10 PM |
| Cheshire | | |
| East Haven | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Daniel Hand | | | | East Shore Athletic Complex - Trail | 11:30 AM |
| Cheshire | | |
| Wilbur Cross | | |
| Sheehan | | |
| Hillhouse | | |
| Amity | | |
| Branford | | |
| Lauralton Hall | | |
| Guilford | | |
| Hamden | | |
| Career Magnet | | |
| West Haven | | |
| North Haven | | |
| Shelton | | |
| East Haven | | |
| Jonathan Law | | |
| Lyman Hall | | |
| Sacred Heart Academy | | |
| Mercy | | |
| MON 10/23 | 3:30 PM | Varsity | Non-League | Normal | Away | Platt Tech | | | | Eisenhower Park - Eisenhower Park | 2:10 PM |
| Jonathan Law | | |
| Lauralton Hall | | |