Head to Head includes singles and doubles results.
| 12/11/20 | Emmanuel Ruiz over John Olcese | 6-4; 6-2 | |
| 11/18/20 | Emmanuel Ruiz over John Olcese | 6-4; 6-0 | |
| 09/23/20 | Emmanuel Ruiz over John Olcese | 6-3; 6-1 | |
| 10/03/19 | Emmanuel Ruiz over John Olcese | 6-3; 6-0 |
