Head to Head includes singles and doubles results.
| 07/15/18 | Phil Harris over Paul Osborne | 6-4; 6-3 | Playoff Match |
| 08/08/15 | Paul Osborne over Phil Harris | 6-3; 6-2 | |
| 05/24/14 | Phil Harris over Paul Osborne |
6-4; 2-6; TB 12-10 |
Playoff Match |
| 10/22/11 | Paul Osborne over Phil Harris | 6-1; 3-6; 6-3 | |
| 04/24/10 | Phil Harris over Paul Osborne |
6-4; 1-6; TB 10-6 |
|
| 11/08/09 | Phil Harris over Paul Osborne | 6-3; 6-3 | Playoff Match |
| 10/03/09 | Phil Harris over Paul Osborne | 6-4; 6-1 | |
| 07/03/09 | Phil Harris over Paul Osborne | 3-6; 6-2; 6-2 | |
| 10/05/08 | Phil Harris over Paul Osborne | 6-2; 6-1 | |
| 08/30/08 | Paul Osborne over Phil Harris | 7-5; 6-3 | |
| 05/10/08 | Phil Harris over Paul Osborne | 3-6; 6-3; 6-0 |
