Quino Munoz defeated Roberto Menendez 6-3 6-4 in the Spain 2 2 round of 32 on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 1–0. Quino Munoz claimed a first win over Roberto Menendez in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-15 | Spain 7 Masters 3 | SF | clay | Roberto Menendez | 6-3 7-5 |