| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/8 | 7:00 p.m. | Varsity | League | Normal | Away | Southington | Loss | 6-7 | | SHS TURF FIELD | |
| FRI 4/10 | 7:00 p.m. | Varsity | League | Normal | Home | Shelton | Win | 12-4 | | Cheshire High Main Game field | |
| MON 4/13 | 5:15 p.m. | Varsity | League | Normal | Away | NotreDame | Loss | 5-8 | | Veteran's Stadium | |
| THU 4/16 | 7:00 p.m. | Varsity | League | Normal | Away | Branford | Loss | 4-7 | | Branford High School-Turf Field | |
| SAT 4/18 | 1:30 p.m. | Varsity | League | Normal | Home | WilliamFloydNY | Loss | 10-11(2OT) | | New Fairfield HS | |
| THU 4/23 | 7:00 p.m. | Varsity | League | Normal | Home | Hamden | Win | 8-7 | | Cheshire High Main Game field | |
| TUE 4/28 | 7:00 p.m. | Varsity | League | Normal | Home | DanielHand | Loss | 5-7 | | Cheshire High Main Game field | |
| THU 4/30 | 7:00 p.m. | Varsity | League | Normal | Home | Conard | Win | 8-7 | | Cheshire High Main Game field | |
| FRI 5/1 | 5:00 p.m. | Varsity | League | Normal | Away | Glastonbury | Loss | 6-14 | | GHS Turf Field | |
| TUE 5/5 | 7:30 p.m. | Varsity | League | Normal | Home | AmityReg | Loss | 7-8 | | Cheshire High Main Game field | |
| THU 5/7 | 5:30 p.m. | Varsity | League | Normal | Away | NorthHaven | Loss | 6-14 | | North Haven Athletic Complex | |
| SAT 5/9 | 4:30 p.m. | Varsity | League | Normal | Away | Guilford | Loss | 7-9 | | Kavanaugh Turf Field at GHS | |
| THU 5/14 | 3:30 p.m. | Varsity | League | Normal | Away | Xavier | Loss | 6-15 | | Xavier H.S. Turf Field | |
| MON 5/18 | 6:30 p.m. | Varsity | League | Normal | Home | FairfieldCollegePreparatory | Loss | 4-16 | | Cheshire High Main Game field | |
| WED 5/20 | 6:00 p.m. | Varsity | League | Normal | Away | Simsbury | Loss | 8-17 | | Simsbury High School - Holden Field (turf) | |
| SAT 5/23 | 12:00 p.m. | Varsity | League | Normal | Away | AndoverMA | Loss | 5-10 | | | |