Stadium: Webster Bank Arena Round: 1
Home Manager: Jay Young Away Manager: Matt McCall
| NCAAB | 2019/11/06 00:00 | UMass Lowell v Massachusetts | W | 64-79 |
| NCAAB | 2019/03/13 17:00 | Massachusetts v George Washington | L | 64-68 |
| NCAAB | 2019/03/09 21:00 | Massachusetts v Rhode Island | L | 75-94 |
| NCAAB | 2019/03/07 00:00 | Richmond v Massachusetts | W | 79-87 |
| NCAAB | 2019/03/02 19:00 | Massachusetts v Duquesne | L | 73-80 |
| NCAAB | 2019/02/27 00:00 | Dayton v Massachusetts | L | 72-48 |
| NCAAB | 2019/02/23 19:00 | St Josephs v Massachusetts | W | 79-80 |
| NCAAB | 2019/02/21 00:00 | Massachusetts v George Washington | L | 67-79 |
| NCAAB | 2019/11/06 00:00 | Bucknell v Fairfield | L | 68-64 |
| NCAAB | 2019/03/08 00:00 | Fairfield v Manhattan | L | 53-57 |
| NCAAB | 2019/03/03 18:00 | Fairfield v St. Peter's | L | 52-62 |
| NCAAB | 2019/03/02 00:00 | Marist v Fairfield | W | 44-59 |
| NCAAB | 2019/02/24 20:30 | Manhattan v Fairfield | W | 59-72 |
| NCAAB | 2019/02/17 19:00 | Fairfield v Niagara | L | 73-78 |
| NCAAB | 2019/02/16 00:00 | Fairfield v Canisius | L | 68-72 |
| NCAAB | 2019/02/09 18:00 | Monmouth v Fairfield | L | 61-49 |