Head to Head includes singles and doubles results.
| 07/04/23 | Lou Friedmann over Robert Raben | 6-4; 6-3 | Playoff Match |
| 06/14/23 | Robert Raben over Lou Friedmann | 6-1; 6-2 | Playoff Match |
| 04/27/23 | Robert Raben over Lou Friedmann | 6-4; 7-5 |
