Head to Head includes singles and doubles results.
| 07/08/23 | Mike Szczupak over Brady Jacob | 6-2; 7-5 | |
| 04/20/23 | Mike Szczupak over Brady Jacob | 6-3; 6-2 | |
| 12/04/22 | Mike Szczupak over Brady Jacob | 6-2; 6-2 | Playoff Match |
| 10/07/22 | Brady Jacob over Mike Szczupak |
6-4; 2-6; TB 10-6 |
|
| 08/26/22 | Mike Szczupak over Brady Jacob | 6-3; 6-0 |
