Head to Head includes singles and doubles results.
| 05/12/24 | Olga Ivanova over James Bryan | 6-3; 7-5 | Playoff Match |
| 04/15/24 | Olga Ivanova over James Bryan |
6-4; 6-7; TB 10-0 |
|
| 01/06/24 | Olga Ivanova over James Bryan | 10-9 | |
| 07/06/23 | Olga Ivanova over James Bryan | 6-1; 6-2 |
