| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/6 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Killingly | | | | Killingly High School - Morgan Field | |
| SAT 9/9 | 11:00 AM | Varsity | Non-League | Normal | Away | Somers/Rockville | Loss | 1-6 | | Somers High School - Somers High School Turf Field | |
| TUE 9/12 | 4:15 PM | Varsity | League | Normal | Home | Stonington | Loss | 1-6 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Home | Norwich Free Academy | Win | 2-1 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| SAT 9/16 | 11:00 AM | Varsity | Non-League | Normal | Away | East Catholic | Win | 1-0 | | East Catholic High School - Lower Field | 12:01 AM |
| FRI 9/22 | 4:15 PM | Varsity | League | Normal | Away | Waterford | Loss | 1-3 | | Waterford High School - Alumni Turf Field/Track | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Home | Killingly | Loss | 0-1 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| THU 9/28 | 6:30 PM | Varsity | League | Normal | Away | East Lyme | Loss | 1-3 | | East Lyme High School - Dick North Turf Field | |
| TUE 10/3 | 4:15 PM | Varsity | League | Normal | Home | Fitch | Loss | 0-3 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| THU 10/5 | 6:30 PM | Varsity | League | Normal | Away | Stonington | Loss | 1-7 | | Stonington High School - Palmer Field (Turf Stadium) | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | Norwich Free Academy | Tied | 0-0 | | Norwich Free Academy - Turf Field | |
| THU 10/12 | 4:15 PM | Varsity | Non-League | Normal | Home | Wethersfield | Loss | 1-5 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| SAT 10/14 | 11:00 AM | Varsity | League | Normal | Home | Valley Regional | Loss | 0-1 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| TUE 10/17 | 4:15 PM | Varsity | League | Normal | Home | Waterford | Loss | 3-4 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| THU 10/19 | 3:00 PM | Varsity | League | Normal | Away | Killingly | Loss | 2-3 | | Killingly High School - Morgan Field | |
| TUE 10/24 | 3:45 PM | Varsity | League | Normal | Home | East Lyme | Loss | 0-6 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| THU 10/26 | 4:00 PM | Varsity | League | Normal | Away | Fitch | Loss | 0-3 | | Groton Middle School - Groton Middle School-Turf Feld | |