Head to Head includes singles and doubles results.
| 09/15/08 | James Cooney over Gary Cahill | 10-7 | |
| 08/23/08 | James Cooney over Gary Cahill | 6-3; 4-6; 7-6 | Playoff Match |
| 08/07/08 | James Cooney over Gary Cahill | 4-6; 6-2; 6-4 | |
| 07/16/08 | James Cooney over Gary Cahill |
5-7; 7-5; TB 10-8 |
