Head to Head includes singles and doubles results.
| 12/13/22 | John Edward Santiago over Bruce Olin | 6-1; 6-3 | |
| 04/22/21 | John Edward Santiago over Bruce Olin | 6-1; 3-6; 6-3 | |
| 03/16/21 | Bruce Olin over John Edward Santiago | 6-2; 6-4 | |
| 01/06/21 | John Edward Santiago over Bruce Olin |
6-3; 4-6; TB 7-6 |
|
| 05/29/20 | Bruce Olin over John Edward Santiago | 7-6; 6-3 | |
| 07/31/19 | John Edward Santiago over Bruce Olin | 6-4; 2-1 Ret. | |
| 07/17/19 | Bruce Olin over John Edward Santiago | 6-1; 6-3 |
