Head to Head includes singles and doubles results.
| 12/20/23 | Ken Ruiz over Robert Phillips | 7-5; 6-2 | Playoff Match |
| 10/19/23 | Ken Ruiz over Robert Phillips | 6-4; 6-4 | |
| 06/07/23 | Ken Ruiz over Robert Phillips | 7-6; 6-0 | |
| 11/01/22 | Ken Ruiz over Robert Phillips | 6-3; 6-3 | |
| 04/11/22 | Robert Phillips over Ken Ruiz | 6-3; 7-6 | |
| 11/28/21 | Ken Ruiz over Robert Phillips |
5-7; 7-6; TB 10-7 |
|
| 05/21/21 | Robert Phillips over Ken Ruiz |
4-6; 6-3; TB 13-11 |
