Ivan Esquerdo defeated Clayton Almeida 6-4 7-6 in the Portugal 1 2 round of 32 on clay. The result followed the form book — Ivan Esquerdo came in leading the head-to-head 1–0. Ivan Esquerdo extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-01 | Portugal 1 3 | R16 | clay | Ivan Esquerdo | 6-2 6-3 |