Stadium: Carl Smith Stadium Round: 1
| NCAAF | 2022/11/12 18:30 | Wingate Bulldogs v Virginia Wise Highland Cavaliers | L | 45-7 |
| NCAAF | 2021/10/23 16:00 | Virginia Wise Highland Cavaliers v Wingate Bulldogs | L | 21-48 |
| NCAAF | 2019/10/26 22:00 | Wingate Bulldogs v Virginia Wise Highland Cavaliers | L | 45-13 |
| NCAAF | 2023/11/04 16:00 | Virginia Wise Highland Cavaliers v Carson–Newman Eagles | L | 7-52 |
| NCAAF | 2023/10/28 17:00 | Mars Hill Lions v Virginia Wise Highland Cavaliers | L | 49-18 |
| NCAAF | 2023/10/21 18:00 | Virginia Wise Highland Cavaliers v Erskine Flying Fleet | W | 34-23 |
| NCAAF | 2023/10/14 18:00 | Tusculum Pioneers v Virginia Wise Highland Cavaliers | L | 35-7 |
| NCAAF | 2023/10/07 18:00 | Virginia Wise Highland Cavaliers v Emory And Henry Wasps | L | 24-41 |
| NCAAF | 2023/09/30 18:00 | Lenoir Rhyne Bears v Virginia Wise Highland Cavaliers | L | 56-3 |
| NCAAF | 2023/09/23 18:00 | Virginia Wise Highland Cavaliers v Limestone Saints | L | 17-38 |
| NCAAF | 2023/09/16 20:00 | Barton Bulldogs v Virginia Wise Highland Cavaliers | L | 28-24 |
| NCAAF | 2023/11/04 17:00 | Newberry Wolves v Wingate Bulldogs | W | 17-21 |
| NCAAF | 2023/10/28 18:00 | Wingate Bulldogs v Lenoir Rhyne Bears | W | 34-30 |
| NCAAF | 2023/10/21 18:00 | Barton Bulldogs v Wingate Bulldogs | W | 24-38 |
| NCAAF | 2023/10/14 19:00 | Wingate Bulldogs v Limestone Saints | L | 10-17 |
| NCAAF | 2023/10/07 22:00 | Catawba College v Wingate Bulldogs | W | 13-31 |
| NCAAF | 2023/09/30 22:00 | Wingate Bulldogs v Erskine Flying Fleet | W | 45-0 |
| NCAAF | 2023/09/23 17:00 | Emory And Henry Wasps v Wingate Bulldogs | W | 10-31 |
| NCAAF | 2023/09/16 22:00 | Wingate Bulldogs v Tusculum Pioneers | L | 21-23 |