Antonio Navarro defeated Roberto Menendez 3-6 7-6 6-2 in the Spain F2 semi-final on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 1–0. Antonio Navarro 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 | R32 | clay | Roberto Menendez | 7-6 3-6 6-1 |