Gabriel Trujillo Soler defeated Oscar Martinez Dieguez 3-6 6-3 6-0 in the Spain F4 round of 32 on clay. The upset overturned the form book — Oscar Martinez Dieguez came in leading the head-to-head 2–0, 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 Oscar Martinez Dieguez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-07 | Spain 5 Masters 1 | R16 | clay | Oscar Martinez Dieguez | 6-2 6-4 |
| 1999-05-07 | Spain 5 Masters 4 | SF | clay | Oscar Martinez Dieguez | 5-7 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.