Head to Head includes singles and doubles results.
| 12/07/22 | Reuben Turtletaub over Derek Dressler | 7-5; 4-6; 6-5 | Playoff Match |
| 10/28/22 | Reuben Turtletaub over Derek Dressler | 6-3; 0-6; 6-4 | |
| 10/30/21 | Derek Dressler over Reuben Turtletaub | 6-2; 6-3 | |
| 04/28/21 | Derek Dressler over Reuben Turtletaub | 6-3; 6-4 | |
| 11/29/20 | Reuben Turtletaub over Derek Dressler | 7-6; 6-0 |
