David Caballero defeated Ivan Esquerdo 6-3 7-5 in the Spain F8 round of 32 on clay. The upset overturned the form book — Ivan Esquerdo came in leading the head-to-head 1–0. David Caballero claimed a first win over Ivan Esquerdo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-08-06 | Spain F5 | R32 | clay | Ivan Esquerdo | 6-4 7-5 |