Head to Head includes singles and doubles results.
| 10/22/21 | Paul Osborne over Ed Cimmino | 6-1; 6-1 | |
| 10/01/21 | Paul Osborne over Ed Cimmino | 6-4; 6-4 | |
| 06/10/18 | Paul Osborne over Ed Cimmino | 6-4; 6-2 | |
| 08/05/17 | Paul Osborne over Ed Cimmino | 6-3; 6-1 | |
| 07/16/17 | Paul Osborne over Ed Cimmino | 6-0; 6-3 |
