Head to Head includes singles and doubles results.
| 10/25/22 | Nat Estes over Brian Kennedy | 6-3; 6-1 | |
| 09/25/22 | Nat Estes over Brian Kennedy | 6-1; 6-1 | |
| 07/31/22 | Nat Estes over Brian Kennedy | 7-5; 6-2 | |
| 10/21/21 | Nat Estes over Brian Kennedy | 6-4; 6-3 |
