Head to Head includes singles and doubles results.
| 11/02/23 | Robert Phillips over Dedric Holmes | 7-6; 6-4 | |
| 10/29/23 | Robert Phillips over Dedric Holmes | 6-3; 6-1 | |
| 05/11/23 | Robert Phillips over Dedric Holmes |
6-4; 4-6; TB 11-9 |
|
| 10/25/20 | Robert Phillips over Dedric Holmes | 7-6; 7-5 | |
| 07/17/20 | Robert Phillips over Dedric Holmes | 6-2; 6-3 | Playoff Match |
| 06/29/20 | Robert Phillips over Dedric Holmes | 7-6; 6-7; 7-6 |
