Head to Head includes singles and doubles results.
| 05/09/23 | John Kyriagis over Jason Williams | 6-3; 6-2 | |
| 04/24/23 | John Kyriagis over Jason Williams | 5-7; 7-6; 1-0 | |
| 10/07/22 | Jason Williams over John Kyriagis | 6-3; 2-6; 6-3 | |
| 08/31/22 | John Kyriagis over Jason Williams | 6-3; 6-3 | |
| 06/17/21 | Jason Williams over John Kyriagis | 6-4; 6-3 | Playoff Match |
| 05/13/21 | John Kyriagis over Jason Williams | 7-5; 7-6 | |
| 09/03/20 | Jason Williams over John Kyriagis | 4-6; 6-2; 6-3 | |
| 08/04/20 | Jason Williams over John Kyriagis | 6-1; 4-6; 7-6 | |
| 06/05/20 | John Kyriagis over Jason Williams | 6-4; 6-4 | |
| 09/11/19 | John Kyriagis over Jason Williams | 6-4; 6-2 | Playoff Match |
| 08/09/19 | John Kyriagis over Jason Williams | 6-2; 3-6; 7-5 | |
| 07/16/19 | Jason Williams over John Kyriagis |
6-2; 4-6; TB 13-11 |
|
| 10/18/18 | Jason Williams over John Kyriagis | 6-4; 2-6; 6-3 | Playoff Match |
