Head to Head includes singles and doubles results.
| 05/23/21 | Jose Medina over Matt Smith | 6-3; 6-3 | |
| 04/17/21 | Jose Medina over Matt Smith | 7-5; 6-1 | Playoff Match |
| 03/08/21 | Jose Medina over Matt Smith | 6-3; 6-3 | |
| 02/20/21 | Jose Medina over Matt Smith | 7-6; 7-6 | |
| 01/10/21 | Jose Medina over Matt Smith | 7-5; 6-3 |
