| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Jonathan Law | | | | Falcon Field (Meriden, CT) - Football Field | 7:00 AM - 2 buses |
| Lyman Hall | | |
| Platt | | |
| THU 9/5 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Bethel | | | | Bethel High School - DeSantis Field at Bethel High | 3:30 PM - 2 buses |
| FRI 9/13 | 7:00 PM | Varsity | League | Normal | Home | Holy Cross | Loss | 15-24 | | Woodland High School - Woodland - Turf Field | |
| FRI 9/20 | 7:00 PM | Varsity | League | Normal | Home | Wolcott | | | | Woodland High School - Woodland - Turf Field | |
| FRI 9/27 | 7:00 PM | Varsity | League | Normal | Home | Crosby | | | | Woodland High School - Woodland - Turf Field | |
| SAT 10/5 | 1:00 PM | Varsity | League | Normal | Away | GNH | | | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | 10:00 AM - Football - 2 buses 10:00am
Cheer - 1 bus 11:00am |
| FRI 10/11 | 6:00 PM | Varsity | League | Normal | Away | Oxford | | | | Oxford High School - OHS Wolverine Field (Turf) | 3:45 PM - Football - 2 buses 3:45pm
Cheer - 1 bus 4:45pm |
| FRI 10/25 | 7:00 PM | Varsity | League | Normal | Home | Naugatuck | | | | Woodland High School - Woodland - Turf Field | |
| FRI 11/1 | 7:00 PM | Varsity | League | Normal | Away | Watertown | | | | Watertown High - John J Mills Complex @ Watertown HS | |
| FRI 11/8 | 6:00 PM | Varsity | League | Normal | Away | Ansonia | | | | Nolan Field-Ansonia - Football Field | 3:45 PM - Football - 2 buses, 3:45pm
Cheer - 1 bus, 4:45pm |
| FRI 11/15 | 7:00 PM | Varsity | League | Normal | Home | Derby | | | | Woodland High School - Woodland - Turf Field | |
| WED 11/27 | 6:00 PM | Varsity | League | Normal | Away | Seymour | | | | Seymour High School - Seymour High School Turf Field | 3:45 PM - Football - 2 buses, 3:45pm
Cheer - 1 bus, 4:45pm |