Head to Head includes singles and doubles results.
| 10/12/23 | Brady Jacob over Bill Gross | 6-2; 6-3 | |
| 11/13/22 | Brady Jacob over Bill Gross | 6-2; 6-2 | Playoff Match |
| 09/02/21 | Brady Jacob over Bill Gross | 6-1; 6-1 | |
| 07/22/21 | Brady Jacob over Bill Gross | 6-3; 6-4 |
