Head to Head includes singles and doubles results.
| 02/07/24 | John Edward Santiago over O.C. Kromby | 6-3; 6-4 | |
| 01/03/24 | O.C. Kromby over John Edward Santiago | 6-3; 4-6; 7-6 | |
| 02/18/22 | O.C. Kromby over John Edward Santiago | 6-1; 6-0 | |
| 03/13/18 | O.C. Kromby over John Edward Santiago | 6-0 |
