Head to Head includes singles and doubles results.
| 04/12/15 | Paul Osborne over Dan Waxman | 6-4; 6-1 | |
| 10/18/14 | Paul Osborne over Dan Waxman | 6-3; 6-3 | |
| 07/20/14 | Paul Osborne over Dan Waxman |
6-4; 4-6; TB 10-6 |
|
| 05/25/14 | Paul Osborne over Dan Waxman | 6-3; 6-2 | |
| 09/21/13 | Paul Osborne over Dan Waxman | 6-0; 6-3 | |
| 08/14/11 | Paul Osborne over Dan Waxman | 7-6; 6-1 | |
| 06/12/11 | Paul Osborne over Dan Waxman | 6-1; 6-2 | |
| 07/03/10 | Paul Osborne over Dan Waxman | 6-3; 6-1 | |
| 06/18/10 | Paul Osborne over Dan Waxman | 6-0; 6-4 | |
| 08/08/08 | Dan Waxman over Paul Osborne |
6-4; 5-7; TB 13-11 |
