Head to Head includes singles and doubles results.
| 10/01/09 | Jay Cottman over Gerard Regan | 4-6; 6-3; 6-4 | |
| 09/29/09 | Jay Cottman over Gerard Regan | 12-10 | |
| 07/25/09 | Gerard Regan over Jay Cottman | 6-7; 6-0; 6-3 | |
| 07/23/09 | Gerard Regan over Jay Cottman | 7-6; 6-2 | |
| 05/21/09 | Jay Cottman over Gerard Regan | 7-5; 6-2 |
