Stadium: George R. Newman Center Round: 1
| NCAAB | 2019/11/16 22:00 | Caldwell v Saint Rose | L | 88-90 |
| NCAAB | 2019/11/14 00:00 | Caldwell v Southern Connecticut State | W | 78-67 |
| NCAAB | 2019/11/09 22:30 | Caldwell v Assumption | L | 73-100 |
| NCAAB | 2019/11/08 21:00 | Caldwell v Saint Michael's | L | 88-114 |
| NCAAB | 2019/03/02 20:00 | Bloomfield v Caldwell | L | 94-86 |
| NCAAB | 2019/02/28 00:30 | Caldwell v Concordia NY | W | 73-66 |
| NCAAB | 2019/02/23 20:00 | Nyack College v Caldwell | W | 53-62 |
| NCAAB | 2019/02/16 20:00 | Caldwell v Holy Family | W | 69-65 |
| NCAAB | 2019/11/17 00:00 | Dominican College v Saint Michael's | L | 89-71 |
| NCAAB | 2019/11/14 00:30 | St Anselm v Saint Michael's | L | 93-72 |
| NCAAB | 2019/11/09 21:00 | NYIT v Saint Michael's | W | 72-77 |
| NCAAB | 2019/11/08 21:00 | Caldwell v Saint Michael's | W | 88-114 |
| NCAAB | 2019/02/27 00:30 | Saint Michael's v Merrimack | L | 72-104 |
| NCAAB | 2019/02/16 20:30 | Saint Michael's v Assumption | W | 76-67 |
| NCAAB | 2019/02/02 20:30 | Saint Michael's v Southern Connecticut State | L | 68-71 |
| NCAAB | 2019/01/31 00:00 | Le Moyne v Saint Michael's | L | 66-63 |