Stadium: David J. Prior Convocation Center Round: 1
| NCAAB | 2019/12/19 00:30 | Tusculum Pioneers v Virginia-Wise Highland Cavaliers | L | 86-84 |
| NCAAB | 2019/12/14 21:00 | Virginia-Wise Highland Cavaliers v Newberry Wolves | L | 67-73 |
| NCAAB | 2019/12/08 02:00 | Catawba Indians v Virginia-Wise Highland Cavaliers | L | 109-87 |
| NCAAB | 2019/11/30 21:00 | Virginia-Wise Highland Cavaliers v Anderson Trojans | W | 90-75 |
| NCAAB | 2019/11/27 00:30 | Virginia-Wise Highland Cavaliers v Mars Hill Lions | L | 87-92 |
| NCAAB | 2019/11/23 00:00 | Virginia-Wise Highland Cavaliers v Alice Lloyd Eagles | W | 88-80 |
| NCAAB | 2019/11/19 00:00 | Virginia-Wise Highland Cavaliers v Berea | W | 100-53 |
| NCAAB | 2019/11/14 00:30 | Samford v Virginia-Wise Highland Cavaliers | L | 102-64 |
| NCAAB | 2019/12/15 21:00 | Oakland City Mighty Oaks v Ohio University Chillcothe Hilltoppers | L | 108-76 |
| NCAAB | 2019/12/14 21:00 | Oakland City Mighty Oaks v Ohio University Chillcothe Hilltoppers | L | 110-61 |
| NCAAB | 2019/11/13 00:00 | Eastern Kentucky v Ohio University Chillcothe Hilltoppers | L | 129-43 |
| NCAAB | 2018/11/30 16:05 | Morehead State v Ohio University Chillcothe Hilltoppers | L | 103-50 |
| NCAAB | 2018/11/18 20:00 | Central State Marauders v Ohio University Chillcothe Hilltoppers | L | 107-84 |