Stadium: Carl Smith Stadium Round: 1
| NCAAF | 2019/10/12 20:00 | Newberry Wolves v Virginia Wise Highland Cavaliers | L | 30-7 |
| NCAAF | 2019/10/05 18:00 | Lenoir Rhyne Bears v Virginia Wise Highland Cavaliers | L | 63-6 |
| NCAAF | 2019/09/28 17:00 | Carson–Newman Eagles v Virginia Wise Highland Cavaliers | L | 42-7 |
| NCAAF | 2019/09/21 16:00 | Virginia Wise Highland Cavaliers v Mars Hill Lions | L | 14-21 |
| NCAAF | 2019/09/14 23:00 | Tennessee Tech v Virginia Wise Highland Cavaliers | L | 31-14 |
| NCAAF | 2019/09/07 16:00 | Virginia Wise Highland Cavaliers v Chowan Hawks | W | 40-22 |
| NCAAF | 2018/11/10 17:00 | Shepherd Rams v Virginia Wise Highland Cavaliers | W | 16-21 |
| NCAAF | 2018/11/03 16:00 | Virginia Wise Highland Cavaliers v Notre Dame Falcons | L | 17-25 |
| NCAAF | 2019/10/12 18:30 | Tusculum Pioneers v Lenoir Rhyne Bears | L | 14-38 |
| NCAAF | 2019/10/05 18:00 | Tusculum Pioneers v Wingate Bulldogs | L | 21-28 |
| NCAAF | 2019/09/28 17:00 | Newberry Wolves v Tusculum Pioneers | L | 30-20 |
| NCAAF | 2019/09/21 17:00 | Limestone Saints v Tusculum Pioneers | W | 10-38 |
| NCAAF | 2019/09/14 22:00 | Tusculum Pioneers v West Alabama Tigers | L | 14-47 |
| NCAAF | 2019/09/06 00:00 | Delta State v Tusculum Pioneers | L | 24-10 |
| NCAAF | 2018/11/10 20:00 | Wingate Bulldogs v Tusculum Pioneers | L | 16-12 |
| NCAAF | 2018/11/03 17:30 | VMI v Tusculum Pioneers | L | 20-11 |