| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Home | Fairfield Prep | | | | West Haven High School - Ken Strong Stadium | |
| O'Brien Tech | | |
| WED 4/10 | 3:45 PM | Varsity | League | Normal | Home | Notre Dame-West Haven | | | | West Haven High School - Ken Strong Stadium | |
| Hamden | | |
| WED 4/17 | 3:45 PM | Varsity | League | Normal | Away | | | | | Hamden High School - HHS Turf #1 | |
| Weaver | | |
| Cheshire | | |
| Amity | | |
| | |
| Hamden | | |
| Career Magnet | | |
| Xavier | | |
| | |
| Notre Dame-West Haven | | |
| Fairfield Prep | | |
| MON 4/22 | 3:45 PM | Varsity | League | Normal | Away | Jonathan Law | | | | Jonathan Law High School - Lawmen Stadium | |
| Foran | | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Away | Branford | | | | Branford High School - Athletic Turf Field | |
| North Haven | | |
| TUE 5/7 | 4:00 PM | Varsity | League | Normal | Away | Career Magnet | | | | Bowen Field - Track | |
| Xavier | | |
| Hillhouse | | |
| THU 5/16 | 3:45 PM | Varsity | League | Normal | Away | Branford | | | | Daniel Hand High School - DHHS Track | |
| Sheehan | | |
| Notre Dame-West Haven | | |
| Foran | | |
| Lyman Hall | | |
| Career Magnet | | |
| Xavier | | |
| Hillhouse | | |
| North Haven | | |
| Wilbur Cross | | |
| East Haven | | |
| Jonathan Law | | |
| Daniel Hand | | |
| Cheshire | | |
| Guilford | | |
| Fairfield Prep | | |
| Hamden | | |
| Shelton | | |
| TUE 5/21 | 1:00 PM | Varsity | Postseason | Normal | Away | Hillhouse | | | | Amity Regional High School - Amity HS Track | |
| Branford | | |
| | |
| Daniel Hand | | |
| Jonathan Law | | |
| Lyman Hall | | |
| Fairfield Prep | | |
| East Haven | | |
| Foran | | |
| North Haven | | |
| Sheehan | | |
| Amity | | |
| Career Magnet | | |
| Hamden | | |
| Wilbur Cross | | |
| Xavier | | |
| Cheshire | | |
| Guilford | | |
| Notre Dame-West Haven | | |
| Shelton | | |