Head to Head includes singles and doubles results.
| 01/19/24 | Nathan Shepherd over Daniel Grajower | 6-2; 7-5 | Playoff Match |
| 12/22/23 | Daniel Grajower over Nathan Shepherd | 6-3; 6-2 | |
| 11/27/23 | Daniel Grajower over Nathan Shepherd | 7-6; 7-5 |
