Head to Head includes singles and doubles results.
| 06/17/23 | Matt Rubenstein over James Cahill | 7-5; 5-7; 6-4 | Playoff Match |
| 05/12/23 | Matt Rubenstein over James Cahill | 7-6; 6-2 | |
| 07/30/22 | Matt Rubenstein over James Cahill | 6-4; 5-7; 6-0 |
