Gabriel Trujillo Soler defeated David Caballero 6-1 7-6 in the Spain F6 round of 16 on clay. The upset overturned the form book — David Caballero came in leading the head-to-head 1–0, but Gabriel Trujillo Soler had been the form player, winning 5 of their last 8 on clay. Gabriel Trujillo Soler claimed a first win over David Caballero 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 | David Caballero | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.