Head to Head includes singles and doubles results.
| 06/24/23 | Ben Stein over Joseph Fennelly | 6-0; 6-3 | |
| 05/14/23 | Ben Stein over Joseph Fennelly | 6-4; 6-3 | Playoff Match |
| 04/24/23 | Ben Stein over Joseph Fennelly | 6-2; 6-2 | |
| 03/16/23 | Ben Stein over Joseph Fennelly | 6-2; 6-2 |
