Guillermo Platel defeated Roberto Menendez 6-7 7-5 6-4 in the Portugal F8 round of 16 on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 1–0. Guillermo Platel claimed a first win over Roberto Menendez in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Bulgaria 1 3 | F | clay | Roberto Menendez | 6-3 6-4 |