| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/28 | Postponed | Varsity | Scrimmage | Postponed | Home | Stafford | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 9/3 | 4:15 PM | Varsity | Non-League | Normal | Home | Lyman Hall | Loss | 1-8 | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| THU 9/5 | 4:15 PM | Varsity | League | Normal | Home | Stonington | Loss | 0-6 | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| SAT 9/7 | 11:00 AM | Varsity | Non-League | Normal | Away | Somers | Loss | 0-4 | | Somers High School - Somers High School Turf Field | |
| TUE 9/10 | 4:15 PM | Varsity | League | Normal | Away | Waterford | Loss | 0-7 | | Waterford High School - Alumni Turf Field/Track | |
| THU 9/12 | 4:15 PM | Varsity | League | Normal | Home | Killingly | Loss | 0-2 | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | NFA | Tied | 1-1 | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| WED 9/18 | 5:00 PM | Varsity | League | Normal | Away | Fitch | Loss | 1-6 | | Groton Middle School - Groton Middle School-Turf Feld | 12:00 PM |
| SAT 9/21 | 3:00 PM | Varsity | Non-League | Normal | Home | Somers | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 9/24 | 6:00 PM | Varsity | League | Normal | Away | East Lyme | | | | East Lyme High School - Dick North Turf Field | |
| THU 9/26 | 4:15 PM | Varsity | Non-League | Normal | Home | East Catholic | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Away | Stonington | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| THU 10/3 | 4:15 PM | Varsity | League | Normal | Home | Waterford | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Killingly | | | | Killingly High School - Morgan Field | |
| THU 10/10 | 4:15 PM | Varsity | League | Normal | Home | Fitch | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |
| TUE 10/15 | 4:00 PM | Varsity | League | Normal | Away | NFA | | | | Norwich Free Academy - Turf Field | |
| THU 10/17 | 4:15 PM | Varsity | League | Normal | Home | East Lyme | | | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | |