| NCAA Division I, FCS, Playoffs | 11/11 17:00 | 1 | Virginia Wise Highland Cavaliers v Wingate Bulldogs | L | 0-27 | |
| NCAA Division I, FCS, Playoffs | 11/04 16:00 | 1 | Virginia Wise Highland Cavaliers v Carson-Newman Eagles | L | 7-52 | |
| NCAA Division I, FCS, Playoffs | 10/28 17:00 | 1 | Mars Hill Lions v Virginia Wise Highland Cavaliers | L | 49-18 | |
| NCAA Division I, FCS, Playoffs | 10/21 18:00 | 1 | Virginia Wise Highland Cavaliers v Erskine Flying Fleet | W | 34-23 | |
| NCAA Division I, FCS, Playoffs | 10/14 18:00 | 1 | Tusculum Pioneers v Virginia Wise Highland Cavaliers | L | 35-7 | |
| NCAA Division I, FCS, Playoffs | 10/07 18:00 | 1 | Virginia Wise Highland Cavaliers v Emory And Henry Wasps | L | 24-41 | |
| NCAA Division I, FCS, Playoffs | 09/30 18:00 | 1 | Lenoir Rhyne Bears v Virginia Wise Highland Cavaliers | L | 56-3 | |
| NCAA Division I, FCS, Playoffs | 09/23 18:00 | 1 | Virginia Wise Highland Cavaliers v Limestone Saints | L | 17-38 | |
| NCAA Division I, FCS, Playoffs | 09/16 20:00 | 1 | Barton Bulldogs v Virginia Wise Highland Cavaliers | L | 28-24 | |
| NCAA Division I, FCS, Playoffs | 09/09 16:00 | 1 | Thomas More Saints v Virginia Wise Highland Cavaliers | L | 37-0 | |
| NCAA Division I, FCS, Playoffs | 09/02 23:00 | 1 | Virginia Wise Highland Cavaliers v Union College Bulldogs | W | 48-0 | |
| NCAA Division I, FCS, Playoffs | 11/12 18:30 | 1 | Wingate Bulldogs v Virginia Wise Highland Cavaliers | L | 45-7 | |
| NCAA Division I, FCS, Playoffs | 11/05 19:00 | 1 | Carson-Newman Eagles v Virginia Wise Highland Cavaliers | L | 38-22 | |
| NCAA Division I, FCS, Playoffs | 10/29 16:00 | 1 | Virginia Wise Highland Cavaliers v Mars Hill Lions | L | 16-20 | |
| NCAA Division I, FCS, Playoffs | 10/22 20:00 | 1 | Erskine Flying Fleet v Virginia Wise Highland Cavaliers | W | 13-28 | |
| NCAA Division I, FCS, Playoffs | 10/15 16:00 | 1 | Virginia Wise Highland Cavaliers v Tusculum Pioneers | L | 9-10 | |
| NCAA Division I, FCS, Playoffs | 10/08 17:00 | 1 | Emory And Henry Wasps v Virginia Wise Highland Cavaliers | L | 34-14 | |
| NCAA Division I, FCS, Playoffs | 09/30 19:00 | 1 | Virginia Wise Highland Cavaliers v Lenoir Rhyne Bears | L | 10-42 | |
| NCAA Division I, FCS, Playoffs | 09/24 23:00 | 1 | Limestone Saints v Virginia Wise Highland Cavaliers | L | 27-13 | |
| NCAA Division I, FCS, Playoffs | 09/17 17:00 | 1 | Virginia Wise Highland Cavaliers v Barton Bulldogs | L | 20-40 | |
| NCAA Division I, FCS, Playoffs | 09/10 23:00 | 1 | North Alabama Lions v Virginia Wise Highland Cavaliers | L | 49-17 | |
| NCAA Division I, FCS, Playoffs | 09/01 23:00 | 1 | Virginia Wise Highland Cavaliers v Ferrum Panthers | W | 41-9 | |
| NCAA Division I, FCS, Playoffs | 11/13 17:00 | 1 | Virginia Wise Highland Cavaliers v Barton Bulldogs | L | 24-36 | |
| NCAA Division I, FCS, Playoffs | 11/06 17:00 | 1 | Catawba v Virginia Wise Highland Cavaliers | W | 7-30 | |
| NCAA Division I, FCS, Playoffs | 10/30 20:00 | 1 | Limestone Saints v Virginia Wise Highland Cavaliers | W | 24-28 | |
| NCAA Division I, FCS, Playoffs | 10/23 16:00 | 1 | Virginia Wise Highland Cavaliers v Wingate Bulldogs | L | 21-48 | |
| NCAA Division I, FCS, Playoffs | 10/16 17:30 | 1 | Tusculum Pioneers v Virginia Wise Highland Cavaliers | L | 37-21 | |
| NCAA Division I, FCS, Playoffs | 10/09 16:00 | 1 | Virginia Wise Highland Cavaliers v Newberry Wolves | L | 14-37 | |
| NCAA Division I, FCS, Playoffs | 10/02 18:00 | 1 | Virginia Wise Highland Cavaliers v Lenoir Rhyne Bears | W | 35-28 | |
| NCAA Division I, FCS, Playoffs | 09/25 16:00 | 1 | Virginia Wise Highland Cavaliers v Carson-Newman Eagles | W | 33-7 |