| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 3/30 | 3:45 p.m. | Varsity | League | Normal | Home | JonathanLaw | Win | 11-10 ot | | HHS Turf Field #1 | |
| TUE 4/2 | 4:00 p.m. | Varsity | League | Normal | Away | Windsor | Loss | 11-12 | | Windsor H.S. | |
| THU 4/4 | 4:30 p.m. | Varsity | League | Normal | Home | NorthHaven | Loss | 20-14 | | HHS Turf Field #1 | |
| SAT 4/6 | 6:00 p.m. | Varsity | League | Normal | Away | WestHaven | Win | 18-6 | | Ken Strong Stadium | |
| WED 4/10 | 4:30 p.m. | Varsity | League | Normal | Home | Shelton | Loss | 10-11(OT) | | HHS Turf Field #1 | |
| THU 4/11 | 4:30 p.m. | Varsity | League | Normal | Home | LymanHall | Win | 11-9 | | HHS Turf Field #1 | |
| TUE 4/16 | 3:45 p.m. | Varsity | League | Normal | Away | AmityReg | Loss | 5-19 | | Amity High School - Field # 3 | |
| TUE 4/23 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 9-13 | | Boyle Stadium, SHS | |
| THU 4/25 | 6:00 p.m. | Varsity | League | Normal | Away | Norwalk | Loss | 11-15 | | Testa Field, NHS | |
| SAT 4/27 | 12:00 p.m. | Varsity | League | Normal | Home | SacredHeartAcademy | Loss | 21-9 | | HHS Turf Field #1 | |
| MON 4/29 | 4:30 p.m. | Varsity | League | Normal | Home | WestHaven | Loss | 8-7 | | HHS Turf Field #1 | |
| FRI 5/3 | 6:00 p.m. | Varsity | League | Normal | Away | Sheehan | Loss | 10-18 | | Sheehan HS Riccitelli Field | |
| MON 5/6 | 6:00 p.m. | Varsity | League | Normal | Away | JonathanLaw | Loss | 7-9 | | Lawmen Stadium | |
| THU 5/9 | 6:30 p.m. | Varsity | League | Normal | Away | LymanHall | Loss | 8-11 | | Lyman Hall Fitzgerald Field | |
| TUE 5/14 | 7:00 p.m. | Varsity | League | Normal | Home | JosephForan | Win | 15-9 | | HHS Turf Field #1 | |
| THU 5/16 | 3:45 p.m. | Varsity | League | Normal | Away | SacredHeartAcademy | Loss | 4-18 | | Sacred Heart Academy | |