Head to Head includes singles and doubles results.
| 04/19/24 | Cullen Tomsheck over Dylan Hopkins | 7-5; 4-6; 6-1 | |
| 04/01/24 | Dylan Hopkins over Cullen Tomsheck | 6-3; 6-4 | |
| 06/26/22 | Dylan Hopkins over Cullen Tomsheck | 6-1; 6-1 | |
| 09/25/21 | Cullen Tomsheck over Dylan Hopkins | 6-4; 3-6; 6-3 |
