| Date | Opponent | Venue | Home/Away | Time | Regis/Opp |
|---|---|---|---|---|---|
| Dec 5 | Inwood Academy | Away | 6:00 PM | 67 - 53 | |
| Dec 6 | Horace Mann | Horace Mann | Away | 68 - 51 | |
| Dec 8 | St. John Prep | St. John's Preparatory School | Away | 6:00 PM | - |
| Dec 13 | Delbarton | Delbarton | Away | 4:00 PM | 33 - 58 |
| Dec 15 | Lasalle | Regis High School | Home | 4:00 PM | 50 - 45 |
| Dec 17 | Cristo Rey | Cristo Rey Brooklyn High School | Away | 5:00 PM | 56 - 42 |
| Dec 22 | Kennedy Catholic | Kennedy Catholic | Away | 3:00 PM | - |
| Dec 29 | Rockhurst (MO) | TAMPA JESUIT HIGH SCHOOL | Away | 2:30 PM | - |
| Dec 30 | TAMPA JESUIT HIGH SCHOOL | Away | - | ||
| Dec 31 | TAMPA JESUIT HIGH SCHOOL | Away | - | ||
| Jan 6 | Cathedral Prep | Regis High School | Home | 4:30 PM | - |
| Jan 8 | Spellman | Regis High School | Home | 6:00 PM | - |
| Jan 9 | Salesian | Salesian High School | Home | 7:30 PM | - |
| Jan 13 | Kennedy Catholic | Regis High School | Away | 5:30 PM | - |
| Jan 14 | Sacred Heart | Regis High School | Home | 4:30 PM | - |
| Jan 17 | Holy Trinity | Regis High School | Home | 1:00 PM | - |
| Jan 21 | Cristo Rey | Regis High School | Home | 5:00 PM | - |
| Jan 23 | Xavier | Xavier High School | Home | 7:00 PM | - |
| Jan 27 | Cathedral Prep | Cathedral Preparatory School and Seminary | Away | 4:30 PM | - |
| Jan 29 | Dwight | Regis High School | Home | 6:15 PM | - |
| Jan 30 | Lasalle | La Salle Academy | Away | 7:15 PM | - |
| Feb 2 | Sacred Heart | Sacred Heart | Away | 4:30 PM | - |
| Feb 4 | Spellman | Cardinal Spellman | Away | 4:30 PM | - |
| Feb 13 | Rye Country Day | Regis High School | Home | 4:45 PM | - |
| Feb 18 | (Varsity Intersectional First Round) | Home | - | ||
| Feb 22 | (Varsity Intersectional Semi-finals) | Home | - | ||
| Feb 27 | (Varsity Intersectional Championship) | Home | - | ||
| Mar 3 | (CHSAA State Tournament ) | Home | - | ||
| Mar 7 | (CHSAA State Tournament ) | Home | - |