Ivan Esquerdo defeated Roberto Menendez 6-7 6-2 6-3 in the Spain F23 round of 32 on hard. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 2–0. Ivan Esquerdo claimed a first win over Roberto Menendez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-07-29 | Spain F8 | SF | clay | Roberto Menendez | 6-4 6-3 |
| 2001-07-09 | Spain F1 | R32 | clay | Roberto Menendez | 6-3 3-6 6-3 |