| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 3:30 PM | Varsity | Scrimmage | Normal | Home | | | | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Main Soccer Field & Track | |
| SAT 9/9 | 9:00 AM | Varsity | Non-League | Normal | Home | Granby Memorial | Loss | 3-7 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Main Soccer Field & Track | |
| FRI 9/15 | 4:00 PM | Varsity | Non-League | Normal | Home | Somers | Win | 2-0 | | The Woodstock Academy - South Campus - Kelly Field & Track | |
| SAT 9/16 | 11:00 AM | Varsity | League | Normal | Home | Killingly | Tied | 0-0 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| TUE 9/19 | 4:15 PM | Varsity | League | Normal | Away | Bacon Academy | Loss | 0-1 | | Bacon Academy - Football/Soccer Field | |
| WED 9/20 | 4:15 PM | Varsity | League | Normal | Home | Waterford | Loss | 0-1 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| SAT 9/23 | 11:00 AM | Varsity | League | Normal | Home | Windham | Loss | 2-3 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Main Soccer Field & Track | |
| SAT 9/30 | 12:30 PM | Varsity | League | Normal | Away | Waterford | Loss | 0-3 | | Waterford High School - Alumni Turf Field/Track | |
| TUE 10/3 | 6:00 PM | Varsity | League | Normal | Away | East Lyme | Loss | 0-3 | | East Lyme High School - Dick North Turf Field | |
| FRI 10/6 | 6:00 PM | Varsity | Non-League | Normal | Away | Lyman Memorial | Win | 7-1 | | Lyman Memorial High School - Soccer Field | |
| TUE 10/10 | 4:15 PM | Varsity | League | Normal | Home | Ledyard | Loss | 1-4 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| THU 10/12 | 7:00 PM | Varsity | League | Normal | Away | Norwich Free Academy | Loss | 2-5 | | Norwich Free Academy - Turf | |
| SAT 10/14 | 11:00 AM | Varsity | League | Normal | Away | Stonington | Loss | 2-8 | | Stonington High School - Palmer Field (Turf Stadium) | |
| MON 10/16 | 4:00 PM | Varsity | League | Normal | Home | Norwich Free Academy | Loss | 0-2 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| WED 10/18 | 4:15 PM | Varsity | League | Normal | Away | Fitch | Loss | 1-3 | | Groton Middle School - Groton Middle School-Turf Feld | |
| FRI 10/20 | 4:15 PM | Varsity | League | Normal | Home | Fitch | Loss | 1-2 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Turf | |
| WED 10/25 | 3:30 PM | Varsity | League | Normal | Home | East Lyme | Loss | 1-6 | | The Woodstock Academy - Charles Bentley Athletic C - Bentley Main Soccer Field & Track | |
| THU 11/2 | 3:00 PM | Varsity | League | Normal | Away | | | | | St. Thomas More School - Soccer Field | |