Head to Head includes singles and doubles results.
| 06/30/09 | Hareesh Rajan over James Gray | 7-5; 7-5 | |
| 06/13/09 | Hareesh Rajan ties James Gray | 1-1 Tie | |
| 05/28/09 | Hareesh Rajan over James Gray |
4-6; 6-4; TB 10-8 |
|
| 05/14/09 | Hareesh Rajan over James Gray | 6-3; 6-1 | |
| 05/06/09 | James Gray over Hareesh Rajan | 6-4; 6-2 | |
| 04/17/09 | James Gray over Hareesh Rajan | 3-6; 6-4; 7-6 | |
| 04/11/09 | James Gray over Hareesh Rajan | 6-1; 4-6; 6-3 | |
| 04/05/09 | Hareesh Rajan over James Gray | 7-5; 1-3 Ret. | |
| 03/25/09 | James Gray ties Hareesh Rajan | 1-1 Tie |
