| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 8:30 AM | Varsity | Scrimmage | Normal | Away | Cheshire | | | | Glastonbury High School - Gym | |
| East Hampton | | |
| Glastonbury | | |
| Maloney | | |
| Hale Ray | | |
| Northwestern | | |
| Rockville | | |
| Suffield | | |
| TUE 9/3 | 5:30 PM | Varsity | Non-League | Normal | Away | Coventry | Win | 3-1 | | Coventry High School - Gym | |
| THU 9/5 | 5:45 PM | Varsity | Non-League | Normal | Away | Wilton | Win | 3-1 | | Wilton High School - Nicholas Zeoli Field House | |
| MON 9/9 | 5:30 PM | Varsity | League | Normal | Home | Griswold | Win | 3-0 | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| WED 9/11 | 5:30 PM | Varsity | League | Normal | Away | Fitch | Win | 3-1 | | Fitch High School - Big Gym | |
| FRI 9/13 | 5:30 PM | Varsity | League | Normal | Away | Plainfield | Win | 3-0 | | Plainfield High School - Gym | |
| WED 9/18 | 5:30 PM | Varsity | League | Normal | Away | East Lyme | Win | 3-1 | | East Lyme High School - North Gym | |
| THU 9/19 | 5:30 PM | Varsity | League | Normal | Home | South Windsor | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| FRI 9/20 | 5:30 PM | Varsity | League | Normal | Home | Waterford | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| MON 9/23 | 5:30 PM | Varsity | League | Normal | Away | NFA | | | | Norwich Free Academy - Alumni Gym | |
| WED 9/25 | 5:30 PM | Varsity | League | Normal | Home | Killingly | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| FRI 9/27 | 5:30 PM | Varsity | League | Normal | Away | Ledyard | | | | Ledyard High School - Judy Standish Gymnasium | |
| MON 9/30 | 5:30 PM | Varsity | Non-League | Normal | Away | Conard | | | | Conard High School - Main Gym | |
| FRI 10/4 | 5:30 PM | Varsity | League | Normal | Home | East Lyme | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| SAT 10/5 | 12:30 PM | Varsity | Non-League | Normal | Home | Glastonbury | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| MON 10/7 | 5:30 PM | Varsity | League | Normal | Away | Waterford | | | | Waterford High School - Francis X. Sweeney Field House | |
| WED 10/9 | 5:30 PM | Varsity | League | Normal | Home | NFA | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| FRI 10/11 | 5:30 PM | Varsity | Non-League | Normal | Home | Newtown | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| MON 10/14 | 6:30 PM | Varsity | League | Normal | Away | Cheshire | | | | Cheshire High School - Gym West | |
| WED 10/16 | 5:30 PM | Varsity | Non-League | Normal | Home | Suffield | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |
| TUE 10/22 | 5:30 PM | Varsity | League | Normal | Home | Lyman Memorial | | | | The Woodstock Academy - North Campus - H208 - Alumni Field House | |