Head to Head includes singles and doubles results.
| 10/07/23 | Max Litvack Winkler over Alex Oberlander | 7-5; 6-3 | |
| 07/27/23 | Max Litvack Winkler over Alex Oberlander | 5-7; 6-2; 6-0 | Playoff Match |
| 06/09/23 | Alex Oberlander over Max Litvack Winkler | 6-3; 6-2 |
