| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/24 | 8:00 AM | Varsity | League | Normal | Away | Holy Cross | | | | Jonathan Law High School - Lawmen Stadium | |
| Jonathan Law | | |
| Foran | | |
| Oxford | | |
| Stamford | | |
| Stratford | | |
| Watertown | | |
| TUE 8/27 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Thomaston | | | | New Fairfield High School - Marty Morgan Field | |
| Jonathan Law | | |
| Danbury | | |
| THU 8/29 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Lakeview | | | | Lakeview High School - Baseball Field | |
| TUE 9/3 | 4:30 PM | Varsity | Non-League | Normal | Away | Daniel Hand | Loss | 0-2 | | Madison Surf Club - Strong Field | |
| THU 9/5 | 6:00 PM | Varsity | League | Normal | Home | Bunnell | Win | 3-2 | | New Fairfield High School - Marty Morgan Field | |
| SAT 9/7 | 10:00 AM | Varsity | League | Normal | Away | Brien McMahon | Loss | 0-4 | | Brien McMahon High School - Pride Field | |
| TUE 9/10 | 6:30 PM | Varsity | League | Normal | Away | Stratford | Win | 6-1 | | Penders Field - Penders Field - Stratford | |
| SAT 9/14 | 10:00 AM | Varsity | Non-League | Normal | Home | New Milford | Win | 1-0 | | New Fairfield High School - Marty Morgan Field | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Immaculate | | | | Immaculate High School - Mustang Valley | |
| THU 9/19 | 6:00 PM | Varsity | League | Normal | Home | Brookfield | | | | New Fairfield High School - Marty Morgan Field | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Away | New Milford | | | | New Milford High School - North Turf Field - NMHS | |
| THU 9/26 | 4:00 PM | Varsity | League | Normal | Home | Notre Dame Prep | | | | New Fairfield High School - Marty Morgan Field | |
| TUE 10/1 | 6:00 PM | Varsity | League | Normal | Away | Newtown | | | | Newtown High School - Blue and Gold Stadium | |
| THU 10/3 | 4:00 PM | Varsity | League | Normal | Home | Kolbe Cathedral | | | | New Fairfield High School - Marty Morgan Field | |
| SAT 10/5 | 3:00 PM | Varsity | League | Normal | Away | Weston | | | | Weston High School - WHS Stadium Field | |
| TUE 10/8 | 6:00 PM | Varsity | League | Normal | Away | Masuk | | | | Masuk High School - Benedict Stadium Field @ Masuk HS | |
| THU 10/10 | 7:00 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Field I (Stadium) | |
| TUE 10/15 | 6:00 PM | Varsity | League | Normal | Home | Bethel | | | | New Fairfield High School - Marty Morgan Field | |
| THU 10/17 | 6:00 PM | Varsity | League | Normal | Home | Pomperaug | | | | New Fairfield High School - Marty Morgan Field | |