Head to Head includes singles and doubles results.
| 09/26/09 | Gerard Regan over Robert Caruso | 6-0; 4-6; 6-0 | |
| 08/23/09 | Gerard Regan over Robert Caruso | 6-2; 7-6 | |
| 07/18/09 | Gerard Regan over Robert Caruso | 7-6; 6-0 | |
| 07/11/09 | Gerard Regan over Robert Caruso | 6-4; 6-1 |
