Head to Head includes singles and doubles results.
| 01/29/24 | John Edward Santiago over David Drill | 7-5; 6-3 | |
| 12/16/22 | David Drill over John Edward Santiago | 6-2; 6-2 | |
| 03/06/22 | David Drill over John Edward Santiago | 6-1; 6-1 |
