Head to Head includes singles and doubles results.
| 01/15/22 | Bobak Massoudi over Roberto Calderon | 6-4; 6-3 | Playoff Match |
| 12/24/21 | Roberto Calderon over Bobak Massoudi | 2-6; 6-0; 6-3 | |
| 04/02/21 | Roberto Calderon over Bobak Massoudi | 6-3; 6-1 | |
| 01/20/21 | Roberto Calderon over Bobak Massoudi | 7-5; 7-6 |
