Stadium: Reitz Arena Round: 1
Home Manager: Tavaras Hardy Away Manager: Brett Nelson
| NCAAB | 2019/01/19 17:05 | Loyola Maryland v Holy Cross | L | 67-65 |
| NCAAB | 2019/01/04 00:00 | Holy Cross v Loyola Maryland | W | 80-73 |
| NCAAB | 2018/02/03 21:00 | Loyola Maryland v Holy Cross | W | 57-73 |
| NCAAB | 2018/01/09 00:05 | Loyola Maryland v Holy Cross | W | 57-64 |
| NCAAB | 2017/02/23 00:05 | Loyola Maryland v Holy Cross | W | 62-63 |
| NCAAB | 2017/01/26 00:30 | Loyola Maryland v Holy Cross | L | 65-62 |
| NCAAB | 2016/03/02 00:30 | Loyola Maryland v Holy Cross | W | 67-72 |
| NCAAB | 2016/02/25 00:30 | Loyola Maryland v Holy Cross | L | 78-63 |
| NCAAB | 2019/12/29 19:00 | Holy Cross v Siena | L | 62-74 |
| NCAAB | 2019/12/22 17:05 | Sacred Heart v Holy Cross | L | 89-68 |
| NCAAB | 2019/12/14 19:00 | Holy Cross v Canisius | L | 72-80 |
| NCAAB | 2019/12/11 00:05 | Holy Cross v Umass Boston | L | 66-69 |
| NCAAB | 2019/12/08 03:00 | Holy Cross v San Diego | L | 51-68 |
| NCAAB | 2019/12/02 16:00 | Mercer v Holy Cross | W | 67-81 |
| NCAAB | 2019/12/01 20:00 | Hofstra v Holy Cross | L | 91-69 |
| NCAAB | 2019/11/30 00:00 | Holy Cross v Florida Atlantic | L | 69-87 |
| NCAAB | 2019/12/29 22:00 | Loyola Maryland v VA Commonwealth | L | 51-85 |
| NCAAB | 2019/12/28 00:00 | UMass Lowell v Loyola Maryland | W | 81-93 |
| NCAAB | 2019/12/21 19:00 | Loyola Maryland v Elizabethtown | W | 72-45 |
| NCAAB | 2019/12/07 21:00 | Loyola Maryland v Mount St Marys | W | 64-48 |
| NCAAB | 2019/12/05 00:00 | Loyola Maryland v Delaware State | W | 84-76 |
| NCAAB | 2019/12/01 23:00 | Binghamton v Loyola Maryland | W | 65-77 |
| NCAAB | 2019/11/27 01:00 | Loyola Maryland v Nebraska Omaha | L | 65-70 |
| NCAAB | 2019/11/25 22:30 | Loyola Maryland v IUPUI | W | 81-77 |