Head to Head includes singles and doubles results.
| 08/11/23 | Trent Chaffee over Jason Williams | 6-2; 6-2 | |
| 07/09/23 | Trent Chaffee over Jason Williams | 6-2; 6-1 | |
| 05/23/23 | Trent Chaffee over Jason Williams | 6-1; 6-3 | |
| 09/06/22 | Trent Chaffee over Jason Williams | 6-0; 6-0 | |
| 06/11/22 | Trent Chaffee over Jason Williams |
7-5; 3-6; TB 10-3 |
|
| 07/18/21 | Trent Chaffee over Jason Williams | 6-1; 6-2 | |
| 07/25/19 | Trent Chaffee over Jason Williams | 6-2; 7-6 | Playoff Match |
| 07/20/16 | Trent Chaffee over Jason Williams | 0-0 Ret. | Playoff Match |
