Head to Head includes singles and doubles results.
| 05/18/23 | Jason Williams over Ross Middleton | 6-2; 6-1 | |
| 04/14/23 | Jason Williams over Ross Middleton | 4-6; 6-0; 6-0 | |
| 09/30/22 | Jason Williams over Ross Middleton | 6-4; 6-2 | |
| 07/16/22 | Jason Williams over Ross Middleton | 7-5; 6-1 | |
| 06/29/22 | Jason Williams over Ross Middleton | 7-5; 6-4 | |
| 05/14/22 | Jason Williams over Ross Middleton | 6-4; 6-2 | |
| 04/22/22 | Jason Williams over Ross Middleton | 6-4; 6-4 | |
| 09/16/21 | Ross Middleton over Jason Williams | 7-6; 6-3 | |
| 07/14/21 | Jason Williams over Ross Middleton | 6-4; 6-1 | |
| 06/16/21 | Jason Williams over Ross Middleton | 4-6; 6-2; 6-1 | |
| 08/02/20 | Jason Williams over Ross Middleton | 6-4; 6-2 | |
| 07/17/20 | Jason Williams over Ross Middleton | 6-2; 6-3 | |
| 06/01/20 | Jason Williams over Ross Middleton | 5-7; 6-2; 6-2 | |
| 08/24/19 | Jason Williams over Ross Middleton | 6-3; 7-6 | |
| 07/24/19 | Jason Williams over Ross Middleton | 6-4; 6-0 | |
| 05/26/19 | Jason Williams over Ross Middleton | 6-4; 6-4 | |
| 05/17/19 | Jason Williams over Ross Middleton | 6-7; 6-4; 6-2 | |
| 08/11/18 | Jason Williams over Ross Middleton | 6-3; 6-2 | |
| 08/03/18 | Jason Williams over Ross Middleton | 6-4; 6-0 | |
| 06/30/18 | Ross Middleton over Jason Williams | 6-4; 6-3 | |
| 07/07/17 | Jason Williams over Ross Middleton | 7-6; 6-3 |
