Head to Head includes singles and doubles results.
| 06/18/09 | Eduardo Castillo over Dale Boutiette | 4-6; 6-1; 6-4 | |
| 03/30/09 | Dale Boutiette over Eduardo Castillo | 6-3; 6-1 | |
| 03/09/09 | Eduardo Castillo over Dale Boutiette | 6-2; 7-5 | |
| 02/27/09 | Dale Boutiette over Eduardo Castillo | 7-5; 3-6; 6-2 | |
| 02/04/09 | Eduardo Castillo over Dale Boutiette | 6-4; 4-6; 6-0 |
