| 2019 CHSAA AA NY Archdiocesan Playoff Bracket | ||||
| QUARTERFINAL | SEMI FINAL | FINAL | ||
| February 17, 2019 | February 19, 2019 | February 23, 2019 | ||
| 1 St. Raymond (19-5) | ||||
| 69-66 | 1 St. Raymond (20-5) | |||
| @ Mount St. Michael | ||||
| 5 Stepinac (10-14) | ||||
| 72-60 | 4 Scanlan (12-13) | |||
| @ St. Raymond HS | ||||
| 4 Scanlan (11-13) | ||||
| 86-65 | 2 Cardinal Hayes (22-5) | |||
| @ Mount St. Michael | Archdiocesan Champion | |||
| 3 Mount St. Michael (15-9) | ||||
| 72-58 | 6 Iona Prep (11-14) | |||
| @ St. Raymond HS | ||||
| 6 Iona Prep (10-14) | ||||
| 12:00 AM | 2 Cardinal Hayes (21-5) | |||
| @ Mount St. Michael | ||||
| 7 St. Peter's (18-6) | ||||
| 78-59 | 2 Cardinal Hayes (20-5) | |||
| @ St. Raymond HS | ||||
| 2 Cardinal Hayes (19-5) | ||||