Roberto Menendez defeated Antonio Navarro 7-6 3-6 6-1 in the Spain 7 Masters 3 round of 32 on clay. The upset overturned the form book — Antonio Navarro came in leading the head-to-head 1–0. Roberto Menendez claimed a first win over Antonio Navarro in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-12 | Spain F2 | SF | clay | Antonio Navarro | 3-6 7-6 6-2 |