| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 3/21 | 4:30 PM | Varsity | Scrimmage | Normal | Home | West Haven | | | | Stamford High School - Boyle Stadium | |
| SUN 3/24 | 8:00 AM | Varsity | Scrimmage | Normal | Away | Bethel | | | | New Milford High School - Joe Wiser Stadium - NMHS | 12:01 AM - 11am departure time for Stamford HS |
| Brookfield | | |
| Danbury | | |
| Fairfield Warde | | |
| Immaculate | | |
| Lewis Mills | | |
| New Fairfield | | |
| New Milford | | |
| Ridgefield | | |
| Trumbull | | |
| Westhill | | |
| THU 3/28 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Joel Barlow HS Stadium | 3:45 PM |
| SAT 3/30 | 10:00 AM | Varsity | League | Normal | Away | Southington | Loss | 6-12 | | Southington High School - 2 TURF FIELD | 7:30 AM |
| THU 4/4 | 6:00 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 12-4 | | Stamford High School - Boyle Stadium | |
| SAT 4/6 | 11:00 AM | Varsity | League | Normal | Away | Danbury | Win | 16-3 | | Danbury High School - Stadium Turf Field | 9:00 AM - JV & V |
| TUE 4/9 | 5:10 PM | Varsity | League | Normal | Away | Greenwich | Loss | 6-14 | | Greenwich High School - Cardinal Stadium | 3:30 PM - JV & V |
| SAT 4/13 | 11:00 AM | Varsity | League | Normal | Home | Brookfield | Win | 14-7 | | Stamford High School - Boyle Stadium | |
| TUE 4/16 | 4:00 PM | Varsity | League | Normal | Home | St. Joseph | Win | 10-7 | | Stamford High School - Boyle Stadium | |
| THU 4/18 | 4:30 PM | Varsity | Non-League | Normal | Home | Norwalk | Loss | 6-10 | | Stamford High School - Boyle Stadium | |
| SAT 4/20 | 12:00 PM | Varsity | League | Normal | Away | Trumbull | Win | 11-7 | | Trumbull High School - McDougall Stadium | 8:00 AM - JV & V |
| THU 4/25 | 5:30 PM | Varsity | League | Normal | Away | Norwalk | Loss | 6-15 | | Nathan Hale MS - Callahan Complex at Nathan Hale Lower | 4:00 PM - Varsity only |
| SAT 4/27 | 10:30 AM | Varsity | Non-League | Normal | Away | Brien McMahon | Win | 10-8 | | Brien McMahon High School - Casagrande Field | 9:00 AM - JV & V |
| MON 4/29 | 4:30 PM | Varsity | Non-League | Normal | Away | Immaculate | Win | 15-1 | | Immaculate High School - Mustang Valley | 2:30 PM |
| WED 5/1 | 4:30 PM | Varsity | League | Normal | Home | Masuk | Loss | 7-12 | | Stamford High School - Boyle Stadium | |
| TUE 5/7 | 4:00 PM | Varsity | League | Normal | Home | Darien | Loss | 2-20 | | Stamford High School - Boyle Stadium | |
| THU 5/9 | 6:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 5-8 | | Fairfield Ludlowe High School - Taft Field | 3:45 PM - Varsity Only |
| SAT 5/11 | 12:00 PM | Varsity | League | Normal | Home | Westhill | Win | 16-4 | | Stamford High School - Boyle Stadium | |
| TUE 5/14 | 4:15 PM | Varsity | League | Normal | Home | Fairfield Warde | Win | 9-7 | | Stamford High School - Boyle Stadium | |
| TUE 5/28 | 5:00 PM | Varsity | Postseason | Normal | Away | Greenwich | Loss | 5-15 | | Greenwich High School - Cardinal Stadium | 3:00 PM |