Head to Head includes singles and doubles results.
| 10/14/19 | John Kilmer over Jason Williams | 6-1; 7-5 | |
| 09/22/19 | Jason Williams over John Kilmer | 6-3; 6-4 | |
| 09/07/19 | Jason Williams over John Kilmer | 7-6; 7-5 | |
| 08/07/19 | Jason Williams over John Kilmer | 7-6; 6-3 | |
| 07/18/19 | Jason Williams over John Kilmer | 6-4; 6-4 |
