Head to Head includes singles and doubles results.
| 10/05/23 | Gregory Gregg over Brett Helberg | 6-4 | |
| 10/01/23 | Brett Helberg over Gregory Gregg |
0-6; 6-3; TB 10-8 |
|
| 09/16/23 | Gregory Gregg ties Brett Helberg | 6-6 Tie | |
| 09/02/23 | Gregory Gregg ties Brett Helberg | 9-7; 4-6; 4-3 Tie | |
| 08/27/23 | Brett Helberg over Gregory Gregg | 9-7; 6-2 |
