Head to Head includes singles and doubles results.
| 04/17/23 | Will Connelly over Jason Williams | 6-2; 6-2 | |
| 07/19/20 | Will Connelly over Jason Williams | 6-1; 6-3 | |
| 09/01/19 | Will Connelly over Jason Williams | 6-2; 5-7; 6-3 | |
| 08/25/19 | Will Connelly over Jason Williams | 6-4; 6-4 | |
| 08/04/19 | Will Connelly over Jason Williams | 6-3; 6-1 | |
| 07/23/19 | Will Connelly over Jason Williams | 6-3; 0-6; 6-2 | |
| 07/14/19 | Jason Williams over Will Connelly | 3-6; 7-5; 7-5 | |
| 06/26/19 | Will Connelly over Jason Williams | 2-6; 7-5; 6-2 | Playoff Match |
| 06/08/19 | Will Connelly over Jason Williams | 6-4; 7-5 | |
| 05/02/19 | Jason Williams over Will Connelly | 6-4; 6-4 |
