Antonio Navarro defeated Gabriel Trujillo Soler 6-3 6-2 in the Spain 3 4 round of 32 on clay. The upset overturned the form book — Gabriel Trujillo Soler came in leading the head-to-head 2–0. Antonio Navarro claimed a first win over Gabriel Trujillo Soler in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Spain F5 | QF | clay | Gabriel Trujillo Soler | 6-4 6-4 |
| 1999-06-04 | Spain 6 Masters 2 | SF | clay | Gabriel Trujillo Soler | 6-7 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.