Stadium: MVP Arena Round: 1
Home Manager: Carmen Maciariello Away Manager: Brett Nelson
| NCAAB | 2018/12/22 17:05 | Siena v Holy Cross | W | 57-60 |
| NCAAB | 2018/11/18 16:00 | Holy Cross v Siena | W | 57-45 |
| NCAAB | 2017/12/23 00:00 | Siena v Holy Cross | L | 71-65 |
| NCAAB | 2008/12/30 12:00 | Holy Cross v Siena | L | 71-83 |
| NCAAB | 2007/12/22 12:00 | Siena v Holy Cross | L | 84-77 |
| NCAAB | 2006/11/18 12:00 | Holy Cross v Siena | W | 65-57 |
| NCAAB | 2005/12/01 12:00 | Siena v Holy Cross | L | 68-63 |
| 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 | 2019/11/23 00:05 | Harvard v Holy Cross | L | 82-74 |
| NCAAB | 2019/12/23 23:00 | Canisius v Siena | W | 72-73 |
| NCAAB | 2019/12/21 23:00 | Bucknell v Siena | W | 71-81 |
| NCAAB | 2019/12/08 03:00 | Siena v Cal Poly SLO | L | 66-70 |
| NCAAB | 2019/11/30 19:00 | Siena v Colgate | L | 62-72 |
| NCAAB | 2019/11/21 00:00 | Siena v Yale | L | 89-100 |
| NCAAB | 2019/11/15 00:00 | Siena v Harvard | L | 56-59 |
| NCAAB | 2019/11/13 00:00 | St. Bonaventure v Siena | W | 65-78 |
| NCAAB | 2019/11/09 00:00 | Siena v Xavier | L | 63-81 |