Head to Head includes singles and doubles results.
| 07/19/23 | Jeremy Bouldin over Jesse Fleming | 0-0 No-Show | |
| 10/13/22 | Jeremy Bouldin over Jesse Fleming | 6-3; 5-7; 6-1 | |
| 06/15/21 | Jeremy Bouldin over Jesse Fleming | 6-4; 6-3 | |
| 09/23/20 | Jesse Fleming over Jeremy Bouldin | 7-5; 6-3 |
