Head to Head includes singles and doubles results.
| 04/08/21 | Sam Ross over Daniel Chippa | 6-3; 6-4 | |
| 03/26/21 | Daniel Chippa over Sam Ross | 6-2; 6-4 | |
| 11/11/20 | Sam Ross over Daniel Chippa |
7-6; 5-7; TB 10-6 |
Playoff Match |
| 07/27/20 | Sam Ross over Daniel Chippa | 6-3; 6-4 |
