| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/6 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Masuk | | | | Masuk High School - David Strong Gymnasium @ Masuk HS | |
| WED 12/27 | 7:45 PM | Varsity | Tournament | Normal | Away | New Fairfield | Loss | 38-54 | | New Fairfield High School - High School Gym | |
| FRI 12/29 | 5:00 PM | Varsity | Tournament | Normal | Home | Weston | Loss | 57-67 | | New Fairfield High School - High School Gym | |
| WED 1/3 | 7:00 PM | Varsity | Non-League | Normal | Away | Bassick | Win | 66-64 | | Bassick High School - Gym | |
| FRI 1/5 | 7:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 55-59 | | Bridgeport Central - Barry McLeod Court | |
| TUE 1/9 | 4:30 PM | Varsity | League | Normal | Away | Ridgefield | Loss | 32-89 | | Ridgefield High School - Main Gym | |
| FRI 1/12 | 7:00 PM | Varsity | League | Normal | Home | Stamford | Loss | 44-63 | | Bridgeport Central - Barry McLeod Court | |
| THU 1/18 | 7:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Loss | 54-60 | | Bridgeport Central - Barry McLeod Court | |
| FRI 1/19 | 7:00 PM | Varsity | League | Normal | Away | Greenwich | Loss | 39-50 | | Greenwich High School - Gymnasium | |
| TUE 1/23 | 7:00 PM | Varsity | League | Normal | Away | Trumbull | Loss | 44-67 | | Trumbull High School - THS Main Gym | |
| FRI 1/26 | 7:00 PM | Varsity | League | Normal | Home | St. Joseph | Loss | 53-65 | | Bridgeport Central - Barry McLeod Court | |
| TUE 1/30 | 7:00 PM | Varsity | League | Normal | Home | Darien | Loss | 62-77 | | Bridgeport Central - Barry McLeod Court | |
| THU 2/1 | 7:00 PM | Varsity | League | Normal | Home | Staples | Loss | 40-67 | | Bridgeport Central - Barry McLeod Court | |
| TUE 2/6 | 7:00 PM | Varsity | League | Normal | Away | Wilton | Loss | 32-63 | | Wilton High School - Nicholas Zeoli Field House | |
| WED 2/7 | 7:00 PM | Varsity | Non-League | Normal | Home | Bassick | Loss | 70-73 | | Bridgeport Central High School - The Barry McLeod Court | |
| FRI 2/9 | 7:00 PM | Varsity | League | Normal | Away | Brien McMahon | Loss | 43-51 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| MON 2/12 | 7:00 PM | Varsity | League | Normal | Home | New Canaan | Loss | 38-56 | | Bridgeport Central - Barry McLeod Court | |
| WED 2/14 | 7:00 PM | Varsity | League | Normal | Home | Westhill | Loss | 44-55 | | Bridgeport Central - Barry McLeod Court | |
| THU 2/15 | 7:00 PM | Varsity | Non-League | Normal | Home | Harding | Loss | 52-63 | | Bridgeport Central High School - The Barry McLeod Court | |
| MON 2/19 | 2:00 PM | Varsity | League | Normal | Away | Danbury | Loss | 42-72 | | Danbury High School - Main Gym | |
| WED 2/21 | 7:00 PM | Varsity | League | Normal | Away | Norwalk | Loss | 32-67 | | Norwalk High School - Tom Scarso Gymnasium | |