Pablo Santos defeated Roberto Menendez 7-6 7-6 in the Spain F21 round of 16 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 |
| 2004-07-05 | Spain F13 | QF | clay | Pablo Santos | 6-4 6-3 |