Head to Head includes singles and doubles results.
| 10/26/23 | Reuben Turtletaub over Serg Makovsky | 6-2; 6-2 | |
| 09/22/20 | Serg Makovsky over Reuben Turtletaub | 7-6; 6-1 | |
| 11/14/18 | Serg Makovsky over Reuben Turtletaub | 6-1; 6-4 | |
| 10/24/18 | Serg Makovsky over Reuben Turtletaub |
4-6; 6-1; TB 10-7 |
