| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/24 | 4:00 PM | Varsity | Scrimmage | Normal | Away | North Haven | | | | North Haven Middle School - East Turf Field | 8:30 AM - 1 Bus |
| MON 8/26 | 5:00 PM | Varsity | Scrimmage | Normal | Home | Xavier | | | | Hamden High School - HHS Turf #2 | |
| THU 8/29 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Xavier | | | | Hamden High School - HHS Turf #2 | |
| SAT 8/31 | 8:00 AM | Varsity | Scrimmage | Normal | Away | Killingly | | | | Sage Park Berlin - Scalise Field | 12:01 AM - 1 Bus |
| Rocky Hill | | |
| South Windsor | | |
| Bacon Academy | | |
| Berlin | | |
| Cromwell | | |
| Wilcox Tech | | |
| Jonathan Law | | |
| TUE 9/3 | 6:00 PM | Varsity | League | Normal | Away | Guilford | Loss | 0-3 | | Guilford High School - Kavanaugh Turf Field and Track | 4:15 PM - 1 Bus |
| FRI 9/6 | 5:00 PM | Varsity | League | Normal | Home | Fairfield Prep | Win | 1-0 | | Hamden High School - HHS Turf #1 | |
| MON 9/9 | 6:30 PM | Varsity | League | Normal | Away | Branford | Loss | 3-6 | | Branford High School - Athletic Turf Field | 2:30 PM - 1 Bus |
| THU 9/12 | 5:00 PM | Varsity | League | Normal | Away | West Haven | Loss | 1-2 | | West Haven High School - Ken Strong Stadium | 3:45 PM - 1 Bus |
| MON 9/16 | 6:00 PM | Varsity | League | Normal | Away | Cheshire | | | | Cheshire High School - Alumni Field - Turf | 4:30 PM - 1 Bus |
| FRI 9/20 | 5:00 PM | Varsity | League | Normal | Home | Foran | | | | Hamden High School - HHS Turf #1 | |
| MON 9/23 | 5:00 PM | Varsity | League | Normal | Home | Amity | | | | Hamden High School - HHS Turf #2 | |
| WED 9/25 | 6:30 PM | Varsity | League | Normal | Away | Career/Hillhouse | | | | Bowen Field - Football Field | 5:00 PM - 1 Bus |
| SAT 9/28 | 11:00 AM | Varsity | League | Normal | Home | Guilford | | | | Hamden High School - HHS Turf #1 | |
| TUE 10/1 | 5:30 PM | Varsity | League | Normal | Away | Fairfield Prep | | | | Fairfield University - Rafferty Stadium | 2:15 PM - 1 Bus |
| SAT 10/5 | 11:00 AM | Varsity | League | Normal | Home | Branford | | | | Hamden High School - HHS Turf #1 | |
| MON 10/7 | 5:00 PM | Varsity | League | Normal | Home | West Haven | | | | Hamden High School - HHS Turf #2 | |
| WED 10/9 | 6:00 PM | Varsity | League | Normal | Home | Cheshire | | | | Hamden High School - HHS Turf #1 | |
| FRI 10/11 | 3:45 PM | Varsity | League | Normal | Away | Foran | | | | Foran High School - Kelley Martin Tighe Memorial Field | 2:15 PM - 1 Bus |
| TUE 10/15 | 4:00 PM | Varsity | League | Normal | Away | Amity | | | | Amity Regional High School - AHS Grass Field # 3 | 2:30 PM - 1 Bus |
| THU 10/17 | 6:00 PM | Varsity | League | Normal | Home | Career/Hillhouse | | | | Hamden High School - HHS Turf #1 | |