Head to Head includes singles and doubles results.
| 02/09/24 | Nathan Shepherd over James Castleberry | 4-6; 6-2; 6-1 | |
| 12/22/23 | James Castleberry over Nathan Shepherd | 7-5; 6-2 | |
| 12/01/23 | Nathan Shepherd over James Castleberry | 6-3; 6-2 | |
| 11/10/23 | Nathan Shepherd over James Castleberry | 6-7; 6-1; 7-5 | |
| 10/08/23 | James Castleberry over Nathan Shepherd | 6-3; 6-3 |
