Roberto Menendez defeated Ivan Esquerdo 6-3 3-6 6-3 in the Spain F1 round of 32 on clay. Roberto Menendez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-09-13 | Spain F23 | R32 | hard | Ivan Esquerdo | 6-7(4) 6-2 6-3 |
| 2002-07-29 | Spain F8 | SF | clay | Roberto Menendez | 6-4 6-3 |