Head to Head includes singles and doubles results.
| 03/06/22 | Chris Ashour over Derek Dressler | 6-3; 7-6 | |
| 01/20/22 | Derek Dressler over Chris Ashour | 10-6 | |
| 01/18/22 | Chris Ashour over Derek Dressler | 10-4 | |
| 12/18/21 | Chris Ashour over Derek Dressler | 6-7; 6-4; 7-6 | |
| 10/08/21 | Chris Ashour over Derek Dressler | 10-7 | |
| 08/06/21 | Derek Dressler over Chris Ashour | 10-5 | |
| 05/22/21 | Derek Dressler over Chris Ashour | 6-2; 0-6; 6-3 |
