Head to Head includes singles and doubles results.
| 05/15/23 | Dillon Grimes over Scott Shapiro | 6-4; 6-4 | |
| 05/14/22 | Scott Shapiro over Dillon Grimes | 6-3; 6-4 | |
| 09/04/21 | Scott Shapiro over Dillon Grimes |
1-6; 6-3; TB 10-6 |
