| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SUN 3/24 | 8:00 AM | Varsity | Scrimmage | Normal | Away | Bethel | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| Brookfield | | |
| Danbury | | |
| Fairfield Warde | | |
| Immaculate | | |
| Lewis Mills | | |
| New Fairfield | | |
| New Milford | | |
| Ridgefield | | |
| Stamford | | |
| Trumbull | | |
| WED 3/27 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Lyman Hall | | | | Westhill High School - Westhill Front Turf Field | |
| SAT 3/30 | 12:00 PM | Varsity | Non-League | Normal | Home | Stratford/Bunnell | Win | 12-0 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 4/2 | 4:30 PM | Varsity | Non-League | Normal | Home | Notre Dame-Fairfield | Win | 13-4 | | Westhill High School - J. Walter Kennedy Stadium | |
| THU 4/4 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Loss | 4-17 | | Westhill High School - J. Walter Kennedy Stadium | |
| SAT 4/6 | 12:00 PM | Varsity | League | Normal | Home | Brien McMahon | Loss | 4-13 | | Westhill High School - J. Walter Kennedy Stadium | |
| THU 4/11 | 6:00 PM | Varsity | League | Normal | Away | Trumbull | Loss | 6-14 | | Trumbull High School - McDougall Stadium | |
| SAT 4/13 | 3:00 PM | Varsity | Non-League | Normal | Away | New Milford | Win | 11-8 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| THU 4/18 | 11:00 AM | Varsity | League | Normal | Away | West Haven | Win | 19-8 | | West Haven High School - Ken Strong Stadium | |
| SAT 4/20 | 10:00 AM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 8-18 | | Fairfield Ludlowe High School - Taft Field | |
| TUE 4/23 | 6:00 PM | Varsity | League | Normal | Away | New Canaan | | | | New Canaan HS - Dunning Stadium | |
| THU 4/25 | 5:30 PM | Varsity | League | Normal | Home | Danbury | Win | 15-5 | | Westhill High School - J. Walter Kennedy Stadium | |
| SAT 5/4 | 12:00 PM | Varsity | League | Normal | Home | Immaculate | Win | 16-4 | | Westhill High School - J. Walter Kennedy Stadium | |
| TUE 5/7 | 5:30 PM | Varsity | League | Normal | Home | Staples | Loss | 5-20 | | Westhill High School - J. Walter Kennedy Stadium | |
| THU 5/9 | 5:30 PM | Varsity | League | Normal | Away | Norwalk | Loss | 8-18 | | Nathan Hale MS - Callahan Complex at Nathan Hale Lower | |
| SAT 5/11 | 12:00 PM | Varsity | League | Normal | Away | Stamford | Loss | 4-16 | | Stamford High School - Boyle Stadium | |
| TUE 5/14 | 5:30 PM | Varsity | League | Normal | Home | St. Joseph | Loss | 9-16 | | Westhill High School - Westhill Front Turf Field | |
| THU 5/16 | 6:00 PM | Varsity | Non-League | Normal | Away | Danbury | Loss | 9-12 | | Danbury High School - Stadium Turf Field | |