Head to Head includes singles and doubles results.
| 10/22/23 | Ben Holland over William Bender | 6-2; 6-2 | |
| 05/09/23 | Ben Holland over William Bender | 6-1; 7-5 | |
| 01/29/23 | William Bender over Ben Holland | 7-5; 6-1 | |
| 06/28/22 | Ben Holland over William Bender |
6-3; 4-6; TB 10-8 |
|
| 09/26/21 | Ben Holland over William Bender | 6-2; 7-5 | |
| 09/24/21 | Ben Holland over William Bender | 6-3; 7-5 | |
| 07/22/17 | Ben Holland over William Bender | 6-3; 6-3 |
