Head to Head includes singles and doubles results.
| 05/16/21 | Charlie Race over John Kyriagis | 6-1; 6-1 | |
| 09/13/20 | John Kyriagis over Charlie Race | 7-6; 7-6 | |
| 07/18/20 | Charlie Race over John Kyriagis | 3-6; 6-3; 6-4 | |
| 05/31/20 | Charlie Race over John Kyriagis | 6-4; 6-1 | |
| 09/14/19 | John Kyriagis over Charlie Race | 7-6; 6-3 | Playoff Match |
| 08/14/19 | John Kyriagis over Charlie Race | 5-7; 6-1; 6-3 |
