Stadium: Pioneer Field Round: 1
| NCAA Division I, FCS, Playoffs | 2022/10/15 16:00 | Virginia Wise Highland Cavaliers v Tusculum Pioneers | W | 9-10 |
| NCAA Division I, FCS, Playoffs | 2021/10/16 17:30 | Tusculum Pioneers v Virginia Wise Highland Cavaliers | W | 37-21 |
| NCAA Division I, FCS, Playoffs | 2019/10/19 17:00 | Virginia Wise Highland Cavaliers v Tusculum Pioneers | W | 19-21 |
| NCAA Division I, FCS, Playoffs | 2023/10/07 17:00 | Carson-Newman Eagles v Tusculum Pioneers | W | 21-27 |
| NCAA Division I, FCS, Playoffs | 2023/09/30 18:00 | Tusculum Pioneers v Barton Bulldogs | L | 14-17 |
| NCAA Division I, FCS, Playoffs | 2023/09/23 20:00 | Tusculum Pioneers v Catawba | W | 35-21 |
| NCAA Division I, FCS, Playoffs | 2023/09/16 22:00 | Wingate Bulldogs v Tusculum Pioneers | W | 21-23 |
| NCAA Division I, FCS, Playoffs | 2023/09/09 18:00 | Virginia State Trojans v Tusculum Pioneers | L | 21-17 |
| NCAA Division I, FCS, Playoffs | 2023/08/31 23:00 | Kennesaw State v Tusculum Pioneers | L | 38-7 |
| NCAA Division I, FCS, Playoffs | 2022/11/12 18:00 | Lenoir Rhyne Bears v Tusculum Pioneers | L | 34-14 |
| NCAA Division I, FCS, Playoffs | 2022/11/05 17:00 | Mars Hill Lions v Tusculum Pioneers | L | 34-27 |
| NCAA Division I, FCS, Playoffs | 2023/10/07 18:00 | Virginia Wise Highland Cavaliers v Emory And Henry Wasps | L | 24-41 |
| NCAA Division I, FCS, Playoffs | 2023/09/30 18:00 | Lenoir Rhyne Bears v Virginia Wise Highland Cavaliers | L | 56-3 |
| NCAA Division I, FCS, Playoffs | 2023/09/23 18:00 | Virginia Wise Highland Cavaliers v Limestone Saints | L | 17-38 |
| NCAA Division I, FCS, Playoffs | 2023/09/16 20:00 | Barton Bulldogs v Virginia Wise Highland Cavaliers | L | 28-24 |
| NCAA Division I, FCS, Playoffs | 2023/09/09 16:00 | Thomas More Saints v Virginia Wise Highland Cavaliers | L | 37-0 |
| NCAA Division I, FCS, Playoffs | 2023/09/02 23:00 | Virginia Wise Highland Cavaliers v Union College Bulldogs | W | 48-0 |
| NCAA Division I, FCS, Playoffs | 2022/11/12 18:30 | Wingate Bulldogs v Virginia Wise Highland Cavaliers | L | 45-7 |
| NCAA Division I, FCS, Playoffs | 2022/11/05 19:00 | Carson-Newman Eagles v Virginia Wise Highland Cavaliers | L | 38-22 |