| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 12/4 | 5:30 PM | Varsity | Scrimmage | Normal | Home | Wilby | | | | Pomperaug High School - Main Gym | |
| WED 12/6 | 5:00 PM | Varsity | Scrimmage | Normal | Away | Naugatuck | | | | Naugatuck High School - Edward Mariano Gymnasium | 4:00 PM |
| MON 12/11 | 5:00 PM | Varsity | Scrimmage | Normal | Away | Nonnewaug | | | | Nonnewaug High School - Gym | 2:15 PM - Share bus w/ JV |
| TUE 12/19 | 7:00 PM | Varsity | Non-League | Normal | Home | Foran | Win | 71-49 | | Pomperaug High School - Main Gym | |
| FRI 12/22 | 7:00 PM | Varsity | Non-League | Normal | Home | Stamford | Loss | 39-48 | | Pomperaug High School - Main Gym | |
| WED 12/27 | 5:00 PM | Varsity | Non-League | Normal | Away | Immaculate | Loss | 46-47 | | Immaculate High School - Immaculate Gym | |
| FRI 12/29 | 3:00 PM | Varsity | Non-League | Normal | Home | West Haven | Loss | 73-89 | | Immaculate High School - Immaculate Gym | |
| THU 1/4 | 7:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | Loss | 53-65 | | Notre Dame - Fairfield - Sister Marion Reilly Auditorium | 4:00 PM - Share bus w/ JV |
| SAT 1/6 | 1:00 PM | Varsity | Non-League | Normal | Home | Jonathan Law | Win | 65-46 | | Pomperaug High School - Main Gym | |
| MON 1/8 | 7:00 PM | Varsity | League | Normal | Away | Stratford | Win | 59-53 | | Stratford High School - Gym | 3:30 PM - Share bus w/ JV |
| THU 1/11 | 7:00 PM | Varsity | League | Normal | Home | Masuk | Loss | 54-56 | | Pomperaug High School - Main Gym | |
| THU 1/18 | 7:00 PM | Varsity | League | Normal | Away | New Milford | Win | 59-48 | | New Milford High School - Main Gym - NMHS | 3:45 PM - Share bus w/ JV |
| FRI 1/19 | 7:00 PM | Varsity | League | Normal | Home | Joel Barlow | Win | 68-43 | | Pomperaug High School - Main Gym | |
| MON 1/22 | 7:00 PM | Varsity | League | Normal | Away | Weston | Win | 47-42 | | Weston High School - Gym (New) | 3:30 PM - Share bus w/ JV |
| FRI 1/26 | 7:00 PM | Varsity | League | Normal | Home | Bethel | Win | 65-45 | | Pomperaug High School - Main Gym | |
| MON 1/29 | 7:00 PM | Varsity | League | Normal | Home | New Fairfield | Win | 63-51 | | Pomperaug High School - Main Gym | |
| THU 2/1 | 7:00 PM | Varsity | League | Normal | Away | Immaculate | Loss | 54-61 | | Immaculate High School - Immaculate Gym | 3:45 PM - Share bus w/ JV |
| MON 2/5 | 7:00 PM | Varsity | League | Normal | Away | Kolbe Cathedral | Loss | 37-65 | | Cardinal Sheehan Center Bridgeport - Cardinal Sheehan Center Bridgeport | 3:45 PM - Share bus w/ JV |
| THU 2/8 | 7:00 PM | Varsity | League | Normal | Home | Brookfield | Win | 62-56 | | Pomperaug High School - Main Gym | |
| SAT 2/10 | 2:30 PM | Varsity | Non-League | Normal | Away | Northwestern | Win | 52-50 | | Northwestern Regional H.S. - Main Gym | 11:30 AM - Share bus w/ JV |
| WED 2/14 | 7:00 PM | Varsity | League | Normal | Away | Newtown | Loss | 55-65 | | Newtown High School - Gym | 5:30 PM - Share bus w/ JV |
| FRI 2/16 | 7:00 PM | Varsity | League | Normal | Home | Bunnell | Loss | 66-73 | | Pomperaug High School - Main Gym | |
| MON 2/19 | 7:00 PM | Varsity | Non-League | Normal | Home | Amity | Loss | 49-52 | | Pomperaug High School - Main Gym | |
| FRI 2/23 | 6:30 PM | Varsity | Postseason | Normal | Away | Kolbe Cathedral | Loss | 47-59 | | Cardinal Sheehan Center Bridgeport - Cardinal Sheehan Center Bridgeport | 4:30 PM |
| MON 3/4 | 6:30 PM | Varsity | Tournament | Normal | Away | Platt Tech | Win | 60-49 | | Platt Tech. - Gym | 4:30 PM |
| WED 3/6 | 6:30 PM | Varsity | Tournament | Normal | Away | Bristol Eastern | Loss | 49-66 | | Bristol Eastern High School - Gym | 4:30 PM |