| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/2 | 10:00 AM | Varsity | Scrimmage | Normal | Away | Ansonia | | | | West Haven High School - Gym | |
| West Haven | | |
| TUE 12/5 | Canceled | Varsity | Scrimmage | Canceled | Away | Sacred Heart Academy | | | | Sacred Heart Academy - Gym | |
| SAT 12/9 | 12:00 PM | Varsity | Scrimmage | Normal | Home | Ridgefield | | | | Immaculate High School - Immaculate Gym | |
| FRI 12/15 | 7:00 PM | Varsity | Non-League | Normal | Away | St. Joseph | Loss | 36-64 | | St. Joseph High School - Gym | |
| MON 12/18 | 7:00 PM | Varsity | Non-League | Normal | Home | Stamford | Win | 60-53 | | Immaculate High School - Immaculate Gym | |
| WED 12/20 | 6:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | Win | 49-46 | | Notre Dame - Fairfield - Sister Marion Reilly Auditorium | |
| TUE 12/26 | 7:30 PM | Varsity | League | Normal | Home | New Fairfield | Win | 45-28 | | Danbury War Memorial - Danbury War Memorial | |
| THU 12/28 | 7:30 PM | Varsity | Non-League | Normal | Away | New Milford | Win | 46-45 | | New Milford High School - Danbury War Memorial | |
| FRI 1/5 | 5:15 PM | Varsity | League | Normal | Home | New Fairfield | Loss | 34-37 | | Immaculate High School - Immaculate Gym | |
| MON 1/8 | 7:00 PM | Varsity | League | Normal | Home | Newtown | Win | 46-42 | | Immaculate High School - Immaculate Gym | |
| THU 1/11 | 7:00 PM | Varsity | League | Normal | Home | Stratford | Win | 58-52 | | Immaculate High School - Immaculate Gym | |
| SAT 1/13 | 11:30 AM | Varsity | Non-League | Normal | Away | Conard | Loss | 33-58 | | Conard High School - Main Gym | |
| FRI 1/19 | 6:00 PM | Varsity | League | Normal | Away | Weston | Win | 56-39 | | Weston High School - Gym (New) | |
| SAT 1/20 | 4:00 PM | Varsity | Non-League | Normal | Home | Fairfield Ludlowe | Loss | 51-55 | | Immaculate High School - Immaculate Gym | |
| THU 1/25 | 7:00 PM | Varsity | League | Normal | Home | Joel Barlow | Win | 49-30 | | Immaculate High School - Immaculate Gym | |
| SAT 1/27 | 1:00 PM | Varsity | League | Normal | Home | Bunnell | Win | 78-26 | | Immaculate High School - Immaculate Gym | |
| MON 1/29 | 7:00 PM | Varsity | League | Normal | Home | Masuk | Loss | 46-57 | | Immaculate High School - Immaculate Gym | |
| THU 2/1 | 7:00 PM | Varsity | League | Normal | Away | Pomperaug | Loss | 38-46 | | Pomperaug High School - Main Gym | |
| SAT 2/3 | 5:00 PM | Varsity | League | Normal | Away | Kolbe Cathedral | Loss | 49-54 | | Cardinal Sheehan Center Bridgeport - Cardinal Sheehan Center Bridgeport | |
| MON 2/5 | 7:00 PM | Varsity | League | Normal | Home | Brookfield | Win | 43-32 | | Immaculate High School - Immaculate Gym | |
| THU 2/8 | 6:00 PM | Varsity | League | Normal | Away | Bethel | Loss | 41-52 | | Bethel High School - BHS gym | |
| SAT 2/10 | 1:45 PM | Varsity | Non-League | Normal | Home | Northwest Catholic | Win | 42-40 | | Immaculate High School - Immaculate Gym | |
| MON 2/12 | 6:00 PM | Varsity | League | Normal | Away | New Milford | Loss | 32-41 | | New Milford High School - Main Gym - NMHS | |
| FRI 2/16 | 6:00 PM | Varsity | Postseason | Normal | Away | New Milford | Loss | 57-60 | | New Milford High School - Main Gym - NMHS | |
| MON 2/26 | 6:30 PM | Varsity | Tournament | Normal | Home | Lewis Mills | Win | 59-38 | | Immaculate High School - Baseball Diamond | |
| THU 2/29 | 6:30 PM | Varsity | Tournament | Normal | Away | St. Paul Catholic | Loss | 47-57 | | St. Paul Catholic HS - Rev. Brian Monnerat Gymnasium | |