Stadium: Irwin Belk Stadium Round: 1
| NCAAF | 2019/10/19 17:30 | Wingate Bulldogs v Unc Pembroke Braves | W | 48-38 |
| NCAAF | 2019/10/12 22:00 | Wingate Bulldogs v Limestone Saints | W | 34-3 |
| NCAAF | 2019/10/05 18:00 | Tusculum Pioneers v Wingate Bulldogs | W | 21-28 |
| NCAAF | 2019/09/28 23:00 | Catawba College v Wingate Bulldogs | W | 10-13 |
| NCAAF | 2019/09/21 22:00 | Wingate Bulldogs v Carson–Newman Eagles | W | 30-28 |
| NCAAF | 2019/09/14 23:00 | Fayetteville State Broncos v Wingate Bulldogs | W | 24-34 |
| NCAAF | 2019/09/05 22:00 | Johnson C Smith GB v Wingate Bulldogs | W | 6-42 |
| NCAAF | 2018/11/24 19:00 | Lenoir Rhyne Bears v Wingate Bulldogs | L | 21-17 |
| NCAAF | 2019/10/19 17:00 | Virginia Wise Highland Cavaliers v Tusculum Pioneers | L | 19-21 |
| 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 |