Stadium: Carl Smith Stadium Round: 1
| NCAAF | 2021/10/16 17:30 | Tusculum Pioneers v Virginia Wise Highland Cavaliers | L | 37-21 |
| NCAAF | 2021/10/09 16:00 | Virginia Wise Highland Cavaliers v Newberry Wolves | L | 14-37 |
| NCAAF | 2021/10/02 18:00 | Virginia Wise Highland Cavaliers v Lenoir Rhyne Bears | W | 35-28 |
| NCAAF | 2021/09/25 16:00 | Virginia Wise Highland Cavaliers v Carson–Newman Eagles | W | 33-7 |
| NCAAF | 2021/09/18 17:00 | Mars Hill Lions v Virginia Wise Highland Cavaliers | L | 44-9 |
| NCAAF | 2021/09/11 23:30 | East Tennessee State v Virginia Wise Highland Cavaliers | L | 45-14 |
| NCAAF | 2021/09/04 16:00 | Virginia Wise Highland Cavaliers v Lynchburg Dragons | W | 54-0 |
| NCAAF | 2019/11/16 18:00 | Unc Pembroke Braves v Virginia Wise Highland Cavaliers | L | 20-7 |
| NCAAF | 2021/10/16 22:00 | Barton Bulldogs v Wingate Bulldogs | L | 26-20 |
| NCAAF | 2021/10/09 17:00 | Limestone Saints v Wingate Bulldogs | W | 17-35 |
| NCAAF | 2021/10/02 22:00 | Wingate Bulldogs v Tusculum Pioneers | W | 43-35 |
| NCAAF | 2021/09/18 17:00 | Carson–Newman Eagles v Wingate Bulldogs | W | 3-25 |
| NCAAF | 2021/09/11 22:00 | Wingate Bulldogs v Fayetteville State Broncos | W | 40-21 |
| NCAAF | 2021/09/02 22:00 | Wingate Bulldogs v Shaw Bears | W | 30-7 |
| NCAAF | 2019/11/23 18:00 | Wingate Bulldogs v West Florida | L | 17-38 |
| NCAAF | 2019/11/16 18:00 | Mars Hill Lions v Wingate Bulldogs | W | 34-64 |