Head to Head includes singles and doubles results.
| 12/05/20 | Evan Cain over Robert Bridge | 6-4; 7-6 | Playoff Match |
| 10/27/20 | Evan Cain over Robert Bridge |
7-6; 4-6; TB 10-4 |
|
| 05/16/20 | Robert Bridge over Evan Cain | 6-4; 7-5 | Playoff Match |
| 03/22/20 | Robert Bridge over Evan Cain | 6-1; 6-4 | |
| 03/15/20 | Evan Cain over Robert Bridge | 6-0; 1-6; 6-1 |
