Head to Head includes singles and doubles results.
| 06/28/14 | Justin Filipowski over Paul Osborne | 7-5; 6-2 | |
| 05/04/14 | Justin Filipowski over Paul Osborne | 7-5; 6-2 | |
| 08/21/11 | Paul Osborne over Justin Filipowski | 6-2; 6-4 | |
| 07/30/11 | Paul Osborne over Justin Filipowski | 6-0; 7-6 | Playoff Match |
| 07/15/11 | Justin Filipowski over Paul Osborne |
2-6; 6-2; TB 11-9 |
|
| 06/18/11 | Paul Osborne over Justin Filipowski | 6-4; 5-0 |
