Head to Head includes singles and doubles results.
| 07/26/23 | Mark Winkelstein over Brian Willey | 1-6; 6-1; 6-4 | Playoff Match |
| 04/16/22 | Brian Willey over Mark Winkelstein |
2-6; 6-3; TB 10-3 |
|
| 04/26/21 | Mark Winkelstein over Brian Willey | 6-2; 6-3 | |
| 03/13/21 | Mark Winkelstein over Brian Willey |
5-7; 6-3; TB 10-5 |
