Head to Head includes singles and doubles results.
| 02/09/24 | Darren Smolkin over William Oliva |
6-3; 3-6; TB 10-4 |
|
| 01/30/24 | Darren Smolkin over William Oliva | 1-6; 6-3; 6-2 | |
| 01/12/24 | William Oliva over Darren Smolkin | 6-4; 2-6; 6-4 | |
| 01/05/24 | Darren Smolkin over William Oliva | 7-6; 7-6 | |
| 12/18/23 | William Oliva over Darren Smolkin | 6-4; 6-1 | |
| 12/08/23 | William Oliva over Darren Smolkin | 6-4; 4-6; 6-2 | Playoff Match |
| 11/06/23 | Darren Smolkin over William Oliva | 6-3; 6-1 | |
| 10/20/23 | Darren Smolkin over William Oliva |
7-6; 2-6; TB 10-8 |
|
| 10/02/23 | William Oliva over Darren Smolkin | 6-3; 6-3 |
