Head to Head includes singles and doubles results.
| 05/25/23 | Tim Condit over Joshua Wintringham | 6-1; 6-3 | |
| 03/02/23 | Tim Condit over Joshua Wintringham | 6-3; 7-5 | Playoff Match |
| 01/23/23 | Tim Condit over Joshua Wintringham | 6-1; 6-1 |
