| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/27 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Windham Tech | | | | Windham Technical High School - Currier Field | 12:00 PM |
| FRI 8/30 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Auburn High School | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTSC - Bentley Soccer Field & Track | |
| TUE 9/3 | 4:15 PM | Varsity | Non-League | Normal | Away | Somers | Loss | 2-7 | | Somers High School - Somers High School Turf Field | 12:00 PM |
| SAT 9/7 | 2:00 PM | Varsity | Non-League | Normal | Away | Berlin | Loss | 1-4 | | Sage Park Berlin - Scalise Field | 12:01 AM |
| TUE 9/10 | 6:30 PM | Varsity | League | Normal | Away | Windham | Loss | 1-2 | | Windham High School - Ferrigno Field | |
| THU 9/12 | 6:00 PM | Varsity | League | Normal | Away | East Lyme | Loss | 3-6 | | East Lyme High School - Dick North Turf Field | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | NFA | Tied | 1-1 | | The Woodstock Academy - Charles Bentley Athletic C - BENTSC - Bentley Soccer Field & Track | |
| THU 9/19 | 4:15 PM | Varsity | League | Normal | Home | Bacon Academy | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTSC - Bentley Soccer Field & Track | |
| SAT 9/21 | 1:00 PM | Varsity | Non-League | Normal | Away | Waterford | | | | Waterford High School - Alumni Turf Field/Track | |
| TUE 9/24 | 4:15 PM | Varsity | League | Normal | Home | Fitch | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Home | Windham | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| THU 10/3 | 7:00 PM | Varsity | League | Normal | Away | Stonington | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| SAT 10/5 | 11:00 AM | Varsity | League | Normal | Home | East Lyme | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 10/8 | 7:00 PM | Varsity | League | Normal | Away | NFA | | | | Norwich Free Academy - Turf Field | |
| THU 10/10 | 4:00 PM | Varsity | League | Normal | Home | Ledyard | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTSC - Bentley Soccer Field & Track | |
| WED 10/16 | 5:15 PM | Varsity | League | Normal | Away | Fitch | | | | Groton Middle School - Groton Middle School-Turf Feld | 12:00 PM |
| SAT 10/19 | 11:00 AM | Varsity | Non-League | Normal | Home | Coventry | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTSC - Bentley Soccer Field & Track | |
| TUE 10/22 | 4:15 PM | Varsity | League | Normal | Home | Waterford | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |