Head to Head includes singles and doubles results.
| 08/02/20 | Irina Bordyn over Caroline Bailey | 6-4; 6-2 | Playoff Match |
| 07/11/20 | Irina Bordyn over Caroline Bailey | 3-6; 6-0; 6-0 | |
| 06/23/20 | Irina Bordyn over Caroline Bailey | 7-5; 6-3 | |
| 06/02/20 | Caroline Bailey over Irina Bordyn |
6-7; 7-6; TB 10-3 |
|
| 05/19/20 | Caroline Bailey over Irina Bordyn | 6-4; 6-4 |
