Ivan Esquerdo defeated David Caballero 6-4 7-5 in the Spain F5 round of 32 on clay. The upset overturned the form book — David Caballero came in leading the head-to-head 1–0. Ivan Esquerdo claimed a first win over David Caballero in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-08-27 | Spain F8 | R32 | clay | David Caballero | 6-3 7-5 |