Stadium: Carl Smith Stadium Round: 1
| NCAAF | 2021/10/16 17:30 | Tusculum Pioneers v Virginia Wise Highland Cavaliers | L | 37-21 |
| NCAAF | 2019/10/19 17:00 | Virginia Wise Highland Cavaliers v Tusculum Pioneers | L | 19-21 |
| NCAAF | 2022/10/08 17:00 | Emory And Henry Wasps v Virginia Wise Highland Cavaliers | L | 34-14 |
| NCAAF | 2022/09/30 19:00 | Virginia Wise Highland Cavaliers v Lenoir Rhyne Bears | L | 10-42 |
| NCAAF | 2022/09/24 23:00 | Limestone Saints v Virginia Wise Highland Cavaliers | L | 27-13 |
| NCAAF | 2022/09/17 17:00 | Virginia Wise Highland Cavaliers v Barton Bulldogs | L | 20-40 |
| NCAAF | 2022/09/10 23:00 | North Alabama v Virginia Wise Highland Cavaliers | L | 49-17 |
| NCAAF | 2022/09/01 23:00 | Virginia Wise Highland Cavaliers v Ferrum Panthers | W | 41-9 |
| NCAAF | 2021/11/13 17:00 | Virginia Wise Highland Cavaliers v Barton Bulldogs | L | 24-36 |
| NCAAF | 2021/11/06 17:00 | Catawba College v Virginia Wise Highland Cavaliers | W | 7-30 |
| NCAAF | 2022/10/08 17:30 | Tusculum Pioneers v Carson–Newman Eagles | W | 34-6 |
| NCAAF | 2022/09/29 21:00 | Barton Bulldogs v Tusculum Pioneers | W | 13-14 |
| NCAAF | 2022/09/24 20:00 | Catawba College v Tusculum Pioneers | W | 17-50 |
| NCAAF | 2022/09/17 22:00 | Tusculum Pioneers v Wingate Bulldogs | L | 10-27 |
| NCAAF | 2022/09/10 17:00 | Chowan Hawks v Tusculum Pioneers | W | 21-23 |
| NCAAF | 2022/09/01 22:00 | Tusculum Pioneers v St Augustines Falcons | W | 70-13 |
| NCAAF | 2021/11/13 18:30 | Tusculum Pioneers v Carson–Newman Eagles | W | 48-13 |
| NCAAF | 2021/11/06 17:00 | Mars Hill Lions v Tusculum Pioneers | L | 20-7 |