Head to Head includes singles and doubles results.
| 01/05/23 | Danny Calise over Ben Holland | 10-7 | |
| 10/18/22 | Danny Calise over Ben Holland | 6-1; 7-5 | |
| 03/22/22 | Danny Calise over Ben Holland | 6-3; 6-4 | |
| 11/16/21 | Danny Calise over Ben Holland | 4-6; 6-3; 6-3 | Playoff Match |
| 09/14/21 | Ben Holland over Danny Calise | 6-4; 7-6 | |
| 06/15/21 | Danny Calise over Ben Holland | 7-6; 6-2 | Playoff Match |
| 05/20/21 | Danny Calise over Ben Holland | 4-6; 6-3; 7-2 |
