Pablo Santos defeated Roberto Menendez 6-4 6-3 in the Spain F13 qualifying round on clay. The result followed the form book — Pablo Santos came in leading the head-to-head 2–1. Pablo Santos extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-11 | Spain F16 | R16 | clay | Pablo Santos | 6-2 6-3 |
| 2004-07-12 | Spain F14 | R32 | clay | Roberto Menendez | 6-1 5-7 6-0 |
| 2003-09-01 | Spain F21 | R16 | clay | Pablo Santos | 7-6(8) 7-6(2) |