Head to Head includes singles and doubles results.
| 01/19/19 | Benjy Cooke over Anthony Valentino | 6-3; 6-3 | |
| 09/08/18 | Anthony Valentino over Benjy Cooke |
7-6; 3-6; TB 10-5 |
|
| 06/30/18 | Benjy Cooke over Anthony Valentino | 6-4; 6-4 | Playoff Match |
| 06/16/18 | Benjy Cooke over Anthony Valentino | 7-5; 6-3 |
