Head to Head includes singles and doubles results.
| 08/21/21 | Jason Kraman over Ben Holland | 6-2; 6-1 | |
| 08/07/21 | Ben Holland over Jason Kraman |
6-4; 0-6; TB 10-6 |
|
| 07/11/21 | Jason Kraman over Ben Holland | 6-4; 6-3 | |
| 10/24/19 | Jason Kraman over Ben Holland | 6-3; 6-1 | Playoff Match |
| 04/10/19 | Jason Kraman over Ben Holland | 6-3; 7-6 | |
| 11/07/18 | Jason Kraman over Ben Holland | 6-3; 7-5 | Playoff Match |
| 09/02/18 | Jason Kraman over Ben Holland | 6-2; 1-6; 6-2 | |
| 05/06/18 | Jason Kraman over Ben Holland | 7-5; 6-0 | |
| 04/22/18 | Jason Kraman over Ben Holland | 6-2; 6-0 | |
| 10/16/17 | Jason Kraman over Ben Holland | 0-0 Ret. | Playoff Match |
| 09/30/17 | Jason Kraman over Ben Holland | 6-2; 3-6; 6-0 | |
| 09/10/17 | Ben Holland over Jason Kraman | 1-6; 6-4; 6-4 | |
| 08/28/17 | Jason Kraman over Ben Holland | 6-3; 7-5 |
