Head to Head includes singles and doubles results.
| 02/17/24 | Jeremy Bouldin over James Leo | 6-4; 6-2 | |
| 08/11/23 | Jeremy Bouldin over James Leo |
1-6; 6-4; TB 10-4 |
|
| 05/26/23 | Jeremy Bouldin over James Leo | 2-6; 6-4; 6-1 | |
| 10/21/22 | Jeremy Bouldin over James Leo | 6-4; 6-3 | Playoff Match |
| 09/24/22 | Jeremy Bouldin over James Leo | 6-2; 7-5 |
