| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 5:00 PM | Varsity | Scrimmage | Normal | Away | Danbury | | | | Danbury High School - Stadium Turf Field | |
| TUE 9/5 | 7:00 PM | Varsity | Scrimmage | Normal | Home | Litchfield | | | | New Fairfield High School - Stadium Field | |
| TUE 9/12 | 6:00 PM | Varsity | League | Normal | Home | Masuk | Loss | 0-3 | | New Fairfield High School - Marty Morgan Field | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Home | Joel Barlow | Tied | 0-0 | | New Fairfield High School - Marty Morgan Field | |
| FRI 9/15 | 4:00 PM | Varsity | Non-League | Normal | Away | Immaculate | Tied | 2-2 | | Immaculate High School - Mustang Valley | |
| TUE 9/19 | 6:00 PM | Varsity | League | Normal | Away | Bunnell | Win | 7-1 | | Bunnell HS - Mastroni Field | |
| THU 9/21 | 6:00 PM | Varsity | League | Normal | Home | Weston | Loss | 0-2 | | New Fairfield High School - Marty Morgan Field | |
| TUE 9/26 | 7:00 PM | Varsity | League | Normal | Away | Pomperaug | Win | 1-0 | | Pomperaug High School - Stadium | |
| THU 9/28 | 4:00 PM | Varsity | League | Normal | Home | Newtown | Win | 2-0 | | New Fairfield High School - Marty Morgan Field | |
| SAT 9/30 | 10:00 AM | Varsity | Non-League | Normal | Away | New Milford | Win | 4-1 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Bethel | Loss | 1-5 | | Bethel High School - MS Turf baseball field | |
| THU 10/5 | 4:15 PM | Varsity | League | Normal | Away | Kolbe Cathedral | Win | 5-0 | | Veterans Memorial Park CT - Veterans Memorial Park CT | |
| SAT 10/7 | 10:00 AM | Varsity | Non-League | Normal | Home | Brien McMahon | Loss | 0-2 | | New Fairfield High School - Stadium Field | |
| TUE 10/10 | 6:00 PM | Varsity | League | Normal | Home | Immaculate | Win | 3-0 | | New Fairfield High School - Marty Morgan Field | |
| THU 10/12 | 5:00 PM | Varsity | League | Normal | Away | Brookfield | Loss | 1-5 | | Brookfield High School - BHS Stadium Field | |
| TUE 10/17 | 6:00 PM | Varsity | League | Normal | Home | Stratford | Win | 3-2 | | New Fairfield High School - Marty Morgan Field | |
| THU 10/19 | 7:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | Loss | 0-2 | | Notre Dame - Fairfield - Park Ave Field | |
| MON 10/23 | 6:00 PM | Varsity | League | Normal | Home | New Milford | Win | 1-0 | | New Fairfield High School - Marty Morgan Field | |
| FRI 10/27 | 5:00 PM | Varsity | Postseason | Normal | Away | Brookfield | | | | Brookfield High School - BHS Stadium Field | |
| THU 11/2 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Joel Barlow | | | | New Fairfield High School - Marty Morgan Field | |
| MON 11/6 | 2:00 PM | Varsity | Postseason | Normal | Away | Nonnewaug | Loss | 1-2 | | Nonnewaug High School - Varsity Field | |