Ivan Esquerdo defeated Clayton Almeida 6-2 6-3 in the Portugal 1 3 round of 16 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 2 | R32 | clay | Ivan Esquerdo | 6-4 7-6(1) |