Kentaro Masuda defeated Ivan Esquerdo 6-1 6-7 6-1 in the Spain F13 round of 32 on hard. The upset overturned the form book — Ivan Esquerdo came in leading the head-to-head 2–0. Kentaro Masuda claimed a first win over Ivan Esquerdo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-08-05 | Spain F9 | R32 | clay | Ivan Esquerdo | 6-3 6-4 |
| 2001-10-09 | Spain F14 | R16 | hard | Ivan Esquerdo | 7-5 6-1 |