Head to Head includes singles and doubles results.
| 09/06/19 | Jack Smith over Timothy VanNasdale | 7-6; 6-3 | |
| 07/19/19 | Jack Smith over Timothy VanNasdale | 6-2; 6-1 | |
| 06/19/19 | Jack Smith over Timothy VanNasdale | 6-4; 7-6 | Playoff Match |
| 05/30/19 | Jack Smith over Timothy VanNasdale | 6-2; 6-4 | |
| 05/23/19 | Jack Smith over Timothy VanNasdale | 6-2; 6-0 | |
| 05/09/19 | Timothy VanNasdale over Jack Smith |
4-6; 6-3; TB 10-7 |
