Head to Head includes singles and doubles results.
| 01/11/24 | Cristian Cisneros Delgado over James Castleberry | 6-4; 6-3 | |
| 11/25/23 | James Castleberry over Cristian Cisneros Delgado | 6-3; 4-6; 6-4 | Playoff Match |
| 10/26/23 | Cristian Cisneros Delgado over James Castleberry | 6-3; 6-3 |
