| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 12/11 | 7:00 PM | Varsity | Non-League | Normal | Home | Pomperaug | Loss | 49-51 | | New Canaan HS - Main Gym | |
| WED 12/13 | 7:00 PM | Varsity | Non-League | Normal | Home | Joel Barlow | Win | 27-25 | | New Canaan HS - Main Gym | |
| SAT 12/16 | 12:15 PM | Varsity | Non-League | Normal | Away | Weston | Win | 42-32 | | Weston High School - Gym (New) | 9:00 AM - 1 Bus - JV/Varsity will ride together |
| WED 12/20 | 5:30 PM | Varsity | Non-League | Normal | Away | Darien | Win | 31-16 | | Darien High School - DHS Main Gym | 2:30 PM - 1 Bus - JV/Varsity will ride together Dattco AT |
| FRI 12/22 | 5:30 PM | Varsity | League | Normal | Home | Trumbull | Win | 45-34 | | New Canaan HS - Main Gym | |
| WED 1/3 | 7:00 PM | Varsity | League | Normal | Away | Ridgefield | Loss | 29-42 | | Ridgefield High School - Main Gym | 3:30 PM - 1 Bus - JV/Varsity will ride together |
| FRI 1/5 | 7:00 PM | Varsity | League | Normal | Home | Danbury | Win | 43-35 | | New Canaan HS - Main Gym | |
| TUE 1/9 | 5:15 PM | Varsity | League | Normal | Away | Staples | Win | 55-50 | | Staples High School - Staples Gym | 4:00 PM - 1 Bus - JV/Varsity will ride together |
| FRI 1/12 | 6:00 PM | Varsity | League | Normal | Home | Norwalk | Win | 46-34 | | New Canaan HS - Main Gym | |
| WED 1/17 | 7:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 43-57 | | New Canaan HS - Main Gym | |
| FRI 1/19 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 33-35 | | Fairfield Warde High School - Large Gym | 3:15 PM - 1 Bus - JV/Varsity will ride together |
| TUE 1/23 | 7:00 PM | Varsity | League | Normal | Away | Greenwich | Loss | 35-40 | | Greenwich High School - Gymnasium | 3:30 PM - 1 Bus - JV/Varsity will ride together |
| FRI 1/26 | 6:00 PM | Varsity | League | Normal | Home | Wilton | Win | 36-29 | | New Canaan HS - Main Gym | |
| TUE 1/30 | 7:00 PM | Varsity | League | Normal | Home | Stamford | Loss | 33-48 | | New Canaan HS - Main Gym | |
| FRI 2/2 | 5:30 PM | Varsity | League | Normal | Home | Darien | Win | 41-21 | | New Canaan HS - Main Gym | |
| MON 2/5 | 6:00 PM | Varsity | Non-League | Normal | Home | Harding | Win | 48-19 | | New Canaan HS - Main Gym | |
| TUE 2/6 | 5:30 PM | Varsity | League | Normal | Away | Brien McMahon | Win | 41-25 | | Brien McMahon High School - Kehoe - King Gymnasium | 2:30 PM - 1 Bus |
| THU 2/8 | 7:00 PM | Varsity | League | Normal | Away | Westhill | Win | 57-12 | | Westhill High School - Main Gym | 4:00 PM - 1 Bus - JV/Varsity will ride together |
| MON 2/12 | 7:00 PM | Varsity | League | Normal | Home | Bridgeport Central | Win | 51-38 | | New Canaan HS - Main Gym | |
| WED 2/14 | 7:00 PM | Varsity | League | Normal | Home | St. Joseph | Loss | 35-42 | | New Canaan HS - Main Gym | |
| SAT 2/17 | 12:45 PM | Varsity | Postseason | Normal | Away | Stamford | | | | Staples High School - Staples Gym | |
| TUE 2/20 | 7:45 PM | Varsity | Postseason | Normal | Away | Ridgefield | | | | Trumbull High School - Gym | |
| THU 2/22 | 7:00 PM | Varsity | Postseason | Normal | Away | St. Joseph | | | | Trumbull High School - Gym | |
| TUE 2/27 | 6:30 PM | Varsity | Tournament | Normal | Home | Guilford | Win | 62-41 | | New Canaan HS - Main Gym | |
| FRI 3/1 | 6:30 PM | Varsity | Tournament | Normal | Away | Masuk | Loss | 32-40 | | Masuk High School - David Strong Gymnasium @ Masuk HS | |