Head to Head includes singles and doubles results.
| 02/12/24 | Jay Chang over Roberto Olivares Amaya | 6-2; 6-3 | Playoff Match |
| 11/19/23 | Jay Chang over Roberto Olivares Amaya | 6-1; 6-3 | Playoff Match |
| 10/25/23 | Jay Chang over Roberto Olivares Amaya | 6-4; 6-2 | |
| 09/18/23 | Jay Chang over Roberto Olivares Amaya | 6-0; 6-0 | Playoff Match |
| 06/14/23 | Jay Chang over Roberto Olivares Amaya | 6-2; 6-1 | |
| 05/18/23 | Jay Chang over Roberto Olivares Amaya |
6-3; 4-6; TB 10-2 |
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| 04/29/23 | Jay Chang over Roberto Olivares Amaya | 6-2; 4-6; 6-3 | Playoff Match |
| 01/25/23 | Jay Chang over Roberto Olivares Amaya | 2-6; 6-0; 6-2 | |
| 01/02/23 | Roberto Olivares Amaya over Jay Chang | 6-3; 0-6; 6-3 |
