Roberto Menendez defeated Pablo Santos 6-1 5-7 6-0 in the Spain F14 round of 32 on clay. The upset overturned the form book — Pablo Santos came in leading the head-to-head 3–0. Roberto Menendez claimed a first win over Pablo Santos in four meetings, narrowing 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 |
| 2004-07-05 | Spain F13 | QF | clay | Pablo Santos | 6-4 6-3 |
| 2003-09-01 | Spain F21 | R16 | clay | Pablo Santos | 7-6(8) 7-6(2) |