Head to Head includes singles and doubles results.
| 04/28/24 | Oscar Rodriguez over John Cropper | 6-2; 6-1 | |
| 07/07/22 | Oscar Rodriguez over John Cropper | 6-1; 7-6 | |
| 05/12/22 | Oscar Rodriguez over John Cropper | 6-0; 6-4 | |
| 08/30/21 | Oscar Rodriguez over John Cropper | 2-6; 7-6; 6-2 | Playoff Match |
| 06/01/21 | Oscar Rodriguez over John Cropper |
3-6; 6-3; TB 10-5 |
|
| 10/10/20 | Oscar Rodriguez over John Cropper | 6-3; 7-5 | |
| 10/03/20 | John Cropper over Oscar Rodriguez |
1-6; 7-5; TB 10-8 |
