Head to Head includes singles and doubles results.
| 09/29/13 | Paul Osborne over Vinay Singh | 0-0 Late Cancellation | |
| 08/10/13 | Paul Osborne over Vinay Singh | 6-3; 3-6; 6-2 | |
| 11/04/12 | Vinay Singh over Paul Osborne | 3-6; 6-3; 6-4 | |
| 06/03/12 | Vinay Singh over Paul Osborne | 6-4; 4-6; 6-4 |
