Head to Head includes singles and doubles results.
| 08/05/21 | Ryan Woodlock over Jeff Kennedy | 6-1; 7-6 | Playoff Match |
| 06/23/21 | Ryan Woodlock over Jeff Kennedy | 6-4; 6-2 | |
| 06/04/21 | Ryan Woodlock over Jeff Kennedy |
6-4; 4-6; TB 10-8 |
