Head to Head includes singles and doubles results.
| 09/10/23 | Caz Novak over Simon You | 6-4; 7-6 | |
| 08/03/23 | Caz Novak over Simon You | 7-5; 6-0 | Playoff Match |
| 05/26/23 | Caz Novak over Simon You | 6-2; 6-0 | Playoff Match |
| 04/23/23 | Simon You over Caz Novak | 1-6; 6-3; 6-3 | |
| 04/14/23 | Caz Novak over Simon You |
6-2; 4-6; TB 10-8 |
