Stadium: Carl Smith Stadium Round: 1
| 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 | 2023/09/09 16:00 | Thomas More Saints v Virginia Wise Highland Cavaliers | L | 37-0 |
| NCAAF | 2023/09/02 23:00 | Virginia Wise Highland Cavaliers v Union College Bulldogs | W | 48-0 |
| NCAAF | 2022/11/12 18:30 | Wingate Bulldogs v Virginia Wise Highland Cavaliers | L | 45-7 |
| NCAAF | 2023/10/14 20:00 | Erskine Flying Fleet v Carson–Newman Eagles | L | 10-14 |
| NCAAF | 2023/10/07 18:30 | Mars Hill Lions v Erskine Flying Fleet | L | 38-3 |
| NCAAF | 2023/09/30 22:00 | Wingate Bulldogs v Erskine Flying Fleet | L | 45-0 |
| NCAAF | 2023/09/23 22:00 | Erskine Flying Fleet v Newberry Wolves | L | 17-24 |
| NCAAF | 2023/09/16 22:00 | Lenoir Rhyne Bears v Erskine Flying Fleet | L | 62-0 |
| NCAAF | 2023/09/09 18:00 | Shorter v Erskine Flying Fleet | L | 28-7 |
| NCAAF | 2023/09/02 23:00 | Allen Yellow Jackets v Erskine Flying Fleet | L | 24-17 |
| NCAAF | 2022/11/12 19:00 | Barton Bulldogs v Erskine Flying Fleet | L | 51-22 |