| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 3/23 | 10:00 AM | Varsity | Scrimmage | Normal | Home | Jonathan Law | | | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 3/26 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Bethel | | | | Westhill High School - J. Walter Kennedy Stadium | |
| THU 4/4 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 5-15 | | Fairfield Warde High School - Tetreau/Davis Field | |
| SAT 4/6 | 10:30 AM | Varsity | League | Normal | Away | Brien McMahon | Win | 8-7 | | Brien McMahon High School - Casagrande Field | |
| THU 4/11 | 4:00 PM | Varsity | League | Normal | Home | Trumbull | Loss | 7-9 | | Westhill High School - J. Walter Kennedy Stadium | |
| SAT 4/13 | 12:00 PM | Varsity | Non-League | Normal | Away | Bunnell/Stratford | Win | 14-0 | | Bunnell HS - Mastroni Field | |
| TUE 4/16 | 4:00 PM | Varsity | Non-League | Normal | Home | Masuk | Loss | 8-18 | | Westhill High School - J. Walter Kennedy Stadium | |
| SAT 4/20 | 12:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 4-16 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Home | New Canaan | Loss | 0-17 | | Westhill High School - J. Walter Kennedy Stadium | |
| THU 4/25 | 4:30 PM | Varsity | League | Normal | Away | Danbury | Win | 9-6 | | Danbury High School - Stadium Turf Field | |
| SAT 4/27 | 1:00 PM | Varsity | Non-League | Normal | Home | Shelton | Win | 4-3 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 4/30 | 4:00 PM | Varsity | Non-League | Normal | Away | Amity | Win | 7-6 | | Amity Regional High School - AHS Grass Field # 3 | |
| SAT 5/4 | 2:00 PM | Varsity | League | Normal | Home | Immaculate | Win | 11-3 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 5/7 | 7:00 PM | Varsity | League | Normal | Away | Staples | Loss | 1-19 | | Staples High School - Staples Stadium | |
| THU 5/9 | 5:30 PM | Varsity | League | Normal | Home | Norwalk | Win | 11-8 | | Westhill High School - J. Walter Kennedy Stadium | |
| SAT 5/11 | 5:15 PM | Varsity | League | Normal | Home | Stamford | Loss | 3-11 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 5/14 | 4:30 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 4-15 | | St. Joseph High School - Upper Turf | |
| WED 5/29 | 4:30 PM | Varsity | League | Normal | Away | Ridgefield | Loss | 1-16 | | Ridgefield High School - Tiger Hollow Stadium | |