| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/6 | 5:30 PM | Varsity | Scrimmage | Normal | Home | Norwich Free Academy | | | | Warren Harding High School - Gym | |
| MON 12/11 | 5:30 PM | Varsity | Scrimmage | Normal | Home | New Canaan | | | | Warren Harding High School - Gym | |
| THU 12/14 | 7:00 PM | Varsity | Non-League | Normal | Home | Wright Tech | Win | 92-23 | | Warren Harding High School - Gym | |
| WED 12/20 | 7:00 PM | Varsity | Non-League | Normal | Away | Fairfield Warde | Loss | 41-81 | | Fairfield Warde High School - Large Gym | |
| FRI 12/22 | 7:00 PM | Varsity | Non-League | Normal | Home | Brien McMahon | Loss | 44-58 | | Warren Harding High School - Gym | |
| WED 12/27 | 3:00 PM | Varsity | League | Normal | Home | Darien | Win | 69-60 | | Warren Harding High School - Gym | |
| WED 1/3 | 7:00 PM | Varsity | Non-League | Normal | Away | Trumbull | Loss | 37-74 | | Trumbull High School - THS Main Gym | |
| SAT 1/6 | 2:00 PM | Varsity | Non-League | Normal | Home | Weston | Loss | 53-54 | | Warren Harding High School - Gym | |
| WED 1/10 | 7:00 PM | Varsity | Non-League | Normal | Home | Stratford | Win | 59-50 | | Warren Harding High School - Gym | |
| SAT 1/13 | 4:00 PM | Varsity | Non-League | Normal | Away | Immaculate | Loss | 64-66 | | Immaculate High School - Baseball Diamond | |
| SAT 1/20 | 12:00 PM | Varsity | Non-League | Normal | Away | Bullard Havens Tech | Win | 46-44 | | Bullard Havens Tech - Gym | |
| FRI 1/26 | 7:00 PM | Varsity | Non-League | Normal | Away | Seymour | Loss | 62-90 | | Seymour Middle School - Gym 1 | |
| WED 1/31 | 7:00 PM | Varsity | Non-League | Normal | Away | Career Magnet | Loss | 44-47 | | Career Magnet - Gym | |
| FRI 2/2 | 7:00 PM | Varsity | Non-League | Normal | Away | Fitch | Loss | 63-74 | | Fitch High School - Big Gym | |
| MON 2/5 | 7:00 PM | Varsity | Non-League | Normal | Home | Wilby | Loss | 70-82 | | Warren Harding High School - Gym | |
| WED 2/7 | 7:00 PM | Varsity | League | Normal | Away | Shepaug Valley | Loss | 62-86 | | Shepaug Valley High School - Ted Alex Gymnasium | |
| SAT 2/10 | 2:00 PM | Varsity | Non-League | Normal | Away | New Britain | Loss | 46-65 | | New Britain High School - Gym | |
| MON 2/12 | 3:30 PM | Varsity | Non-League | Normal | Home | Career Magnet | Loss | 52-56 | | Warren Harding High School - Gym | |
| THU 2/15 | 7:00 PM | Varsity | Non-League | Normal | Away | Bridgeport Central | Win | 63-52 | | Bridgeport Central High School - The Barry McLeod Court | |
| FRI 2/16 | 7:00 PM | Varsity | Non-League | Normal | Away | Valley Regional | Win | 57-39 | | Valley Regional High School - Valley Regional High School Gym | |
| THU 2/22 | 7:00 PM | Varsity | Non-League | Normal | Away | Bassick | Win | 79-71 | | Bassick High School - Gym | |
| FRI 2/23 | 7:00 PM | Varsity | Non-League | Normal | Home | Amistad | Win | 81-62 | | Warren Harding High School - Gym | |
| THU 2/29 | 4:45 PM | Varsity | Scrimmage | Normal | Away | New Canaan | | | | New Canaan HS - Main Gym | |
| TUE 3/5 | 6:30 PM | Varsity | Tournament | Normal | Away | Shepaug Valley | Loss | 60-70 | | Shepaug Valley High School - Ted Alex Gymnasium | |