| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 12/5 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Abbott Tech | | | | Abbott V-T School - Daniel A. Garamella Memorial Gymnasium | |
| THU 12/7 | 5:00 PM | Varsity | Scrimmage | Normal | Home | Kolbe Cathedral | | | | Brien McMahon High School - Kehoe - King Gymnasium | |
| MON 12/11 | 5:15 PM | Varsity | League | Normal | Away | Guilford | Loss | 35-37 | | Guilford High School - Main gym at GHS | |
| MON 12/18 | 6:00 PM | Varsity | Non-League | Normal | Home | Harding | Win | 59-37 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| FRI 12/22 | 5:30 PM | Varsity | League | Normal | Home | Fairfield Warde | Loss | 40-53 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| WED 12/27 | 12:00 PM | Varsity | Non-League | Normal | Home | Joel Barlow | Loss | 29-41 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| WED 1/3 | 5:30 PM | Varsity | League | Normal | Home | Darien | Win | 44-35 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| FRI 1/5 | 5:30 PM | Varsity | League | Normal | Home | Greenwich | Win | 42-38 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| TUE 1/9 | 5:30 PM | Varsity | League | Normal | Away | Stamford | Loss | 37-64 | | Stamford High School - Kuczo Gymnasium | |
| FRI 1/12 | 5:30 PM | Varsity | League | Normal | Home | Staples | Loss | 29-52 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| WED 1/17 | 6:30 PM | Varsity | League | Normal | Away | Trumbull | Loss | 26-43 | | Trumbull High School - THS Main Gym | |
| FRI 1/19 | 6:00 PM | Varsity | League | Normal | Away | Danbury | Loss | 36-58 | | Danbury High School - Main Gym | |
| TUE 1/23 | 5:30 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 44-63 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| FRI 1/26 | 5:30 PM | Varsity | League | Normal | Home | Westhill | Win | 67-17 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| TUE 1/30 | 7:00 PM | Varsity | League | Normal | Away | Ridgefield | Loss | 31-54 | | Ridgefield High School - Main Gym | |
| FRI 2/2 | 5:15 PM | Varsity | League | Normal | Home | Norwalk | Loss | 35-62 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| TUE 2/6 | 5:30 PM | Varsity | League | Normal | Home | New Canaan | Loss | 25-41 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| FRI 2/9 | 7:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 43-36 | | Bridgeport Central - Barry McLeod Court | |
| MON 2/12 | 7:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 29-48 | | St. Joseph High School - Gym | |
| WED 2/14 | 6:00 PM | Varsity | League | Normal | Away | Wilton | Loss | 28-48 | | Wilton High School - Nicholas Zeoli Field House | |
| FRI 2/16 | 6:00 PM | Varsity | Non-League | Normal | Away | Harding | Win | 69-32 | | Warren Harding High School - Gym | |
| MON 2/19 | 12:00 PM | Varsity | Non-League | Normal | Home | Bassick | Win | 49-47 | | Brien McMahon High School - Kehoe - King Gymnasium | |
| MON 2/26 | 6:00 PM | Varsity | Tournament | Normal | Away | New London | Loss | 31-71 | | New London High School - Conway Gym | |