| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/8 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-21 | | DHS Turf #2 | |
| SAT 4/11 | 7:00 p.m. | Varsity | League | Normal | Away | Brookfield | Loss | 12-2 | | BHS Stadium Field | |
| TUE 4/14 | 5:30 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 4-18 | | Brien McMahon HS | |
| THU 4/16 | 5:30 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 15-0 | | Westhill Front Field | |
| TUE 4/21 | 4:15 p.m. | Varsity | League | Normal | Away | Immaculate | Loss | 9-10 | | Mustang Valley | |
| THU 4/23 | 5:30 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 1-12 | | Westhill Front Turf Field | |
| SAT 4/25 | 3:00 p.m. | Varsity | League | Normal | Away | Bethel | Loss | 1-11 | | DeSantis Field at Bethel High School | |
| TUE 4/28 | 6:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 4-13 | | McDougall Stadium | |
| SAT 5/2 | 5:00 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 10-3 | | Danbury High School Stadium | |
| MON 5/4 | 5:30 p.m. | Varsity | League | Normal | Home | KingLowHeywoodThomas | Loss | 11-7 | | Westhill Front Field | |
| THU 5/7 | 5:30 p.m. | Varsity | League | Normal | Home | Stamford | Win | 11-10 | | Westhill Front Turf Field | |
| SAT 5/9 | 1:00 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 3-16 | | St. Joseph High School | |
| TUE 5/12 | 6:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 20-2 | | Tiger Hollow Stadium | |
| THU 5/14 | 5:30 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 14-0 | | Westhill Front Turf Field | |
| SAT 5/16 | 10:00 a.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 14-3 | | Westhill Front Field | |
| TUE 5/19 | 5:30 p.m. | Varsity | League | Normal | Home | Staples | Loss | 17-3 | | Westhill Front Turf Field | |