Head to Head includes singles and doubles results.
| 09/29/23 | Jeff Segal over Dylan Hopkins | 6-1; 4-6; 6-4 | |
| 05/18/23 | Jeff Segal over Dylan Hopkins | 3-6; 7-6; 6-4 | Playoff Match |
| 05/01/23 | Dylan Hopkins over Jeff Segal | 6-4; 6-4 |
