Head to Head includes singles and doubles results.
| 10/19/19 | Sam Anneken over Nathan Hertlein | 6-1; 6-4 | Playoff Match |
| 10/13/19 | Sam Anneken over Nathan Hertlein | 4-6; 6-1; 6-4 | |
| 09/17/19 | Nathan Hertlein over Sam Anneken | 6-3; 0-6; 6-3 |
