Head to Head includes singles and doubles results.
| 04/27/24 | Kenneth Kawahara over Tim Bradley | 6-0; 6-2 | |
| 04/10/24 | Kenneth Kawahara over Tim Bradley | 6-0; 3-6; 6-3 | |
| 05/30/23 | Kenneth Kawahara over Tim Bradley | 6-3; 7-6 | |
| 05/10/23 | Kenneth Kawahara over Tim Bradley | 2-6; 6-4; 6-3 | |
| 04/08/23 | Kenneth Kawahara over Tim Bradley | 2-6; 7-5; 6-2 | |
| 11/03/22 | Tim Bradley over Kenneth Kawahara | 2-6; 6-2; 6-3 |
