| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 12/1 | 4:00 PM | Varsity | Scrimmage | Normal | Home | | | | | Windsor High School - WHS Main Gym | |
| WED 12/6 | 3:30 PM | Varsity | Scrimmage | Normal | Away | Northwest Catholic | | | | Northwest Catholic High School (Primary) - Johnson Gym | 12:01 AM |
| TUE 12/12 | 6:45 PM | Varsity | League | Normal | Home | Enfield | Loss | 40-41 | | Windsor High School - WHS Main Gym | |
| FRI 12/15 | 6:45 PM | Varsity | League | Normal | Home | Glastonbury | Loss | 41-53 | | Windsor High School - WHS Main Gym | |
| TUE 12/19 | 6:45 PM | Varsity | League | Normal | Away | Southington | Win | 56-53 | | Southington High School - Gym West | |
| FRI 12/22 | 5:30 PM | Varsity | League | Normal | Home | Newington | Loss | 45-52 | | Windsor High School - WHS Main Gym | |
| FRI 12/29 | 1:30 PM | Varsity | League | Normal | Away | Hamden | Loss | 36-58 | | Hamden High School - HHS Gym | |
| WED 1/3 | 5:30 PM | Varsity | League | Normal | Away | Hartford Public | Win | 70-14 | | Hartford Public High School - Field House | |
| FRI 1/5 | 6:45 PM | Varsity | League | Normal | Away | E.O. Smith | Loss | 56-61 | | E.O. Smith High School - Front Gym | |
| MON 1/8 | 6:45 PM | Varsity | League | Normal | Home | East Hartford | Win | 46-42 | | Windsor High School - WHS Main Gym | |
| WED 1/10 | 6:45 PM | Varsity | League | Normal | Home | Holy Cross | Loss | 59-65 | | Windsor High School - WHS Main Gym | |
| FRI 1/12 | 6:45 PM | Varsity | League | Normal | Away | New Britain | Win | 56-27 | | New Britain High School - Gym | |
| WED 1/17 | 5:15 PM | Varsity | League | Normal | Away | Manchester | Win | 65-47 | | Manchester High School - Gym | |
| FRI 1/19 | 5:30 PM | Varsity | League | Normal | Home | Berlin | Win | 41-37 | | Windsor High School - WHS Main Gym | |
| SAT 1/20 | 11:00 AM | Varsity | League | Normal | Home | Somers | Win | 64-43 | | Windsor High School - WHS Main Gym | |
| WED 1/24 | 6:45 PM | Varsity | League | Normal | Away | Simsbury | Loss | 39-46 | | Simsbury High School - Simsbury / Main Gym | |
| FRI 1/26 | 5:30 PM | Varsity | League | Normal | Away | Newington | Win | 51-42 | | Newington High School - Newington | |
| FRI 2/2 | 5:30 PM | Varsity | League | Normal | Home | RHAM | Win | 62-42 | | Windsor High School - WHS Main Gym | |
| TUE 2/6 | 6:45 PM | Varsity | League | Normal | Home | Rocky Hill | Win | 67-50 | | Windsor High School - WHS Main Gym | |
| WED 2/7 | 5:30 PM | Varsity | Non-League | Normal | Home | Wilbur Cross | Win | 92-30 | | Windsor High School - WHS Main Gym | |
| FRI 2/9 | 6:45 PM | Varsity | League | Normal | Home | Wethersfield | Win | 87-18 | | Windsor High School - WHS Main Gym | |
| MON 2/12 | 5:30 PM | Varsity | League | Normal | Away | Bloomfield | Win | 89-32 | | Bloomfield High School - Main Gym | |
| THU 2/15 | 6:30 PM | Varsity | Postseason | Normal | Away | E.O. Smith | Win | 65-46 | | E.O. Smith High School - Front Gym | |
| SAT 2/17 | 1:00 PM | Varsity | Postseason | Normal | Away | Newington | Win | 51-33 | | Plainville High School - Wood Gymnasium | |
| TUE 2/27 | 6:00 PM | Varsity | Tournament | Normal | Home | Notre Dame-Fairfield | Win | 56-32 | | Windsor High School - WHS Main Gym | |
| FRI 3/1 | 6:30 PM | Varsity | Tournament | Normal | Away | Woodstock Academy | Win | 59-39 | | The Woodstock Academy - North Campus - Alumni Field House Main Court | |
| TUE 3/5 | 7:00 PM | Varsity | Tournament | Normal | Away | Simsbury | Loss | 31-37 | | Simsbury High School - Simsbury / Main Gym | |