Oscar Martinez Dieguez defeated Gabriel Trujillo Soler 5-7 6-4 7-5 in the Spain 5 Masters 4 semi-final on clay. Oscar Martinez Dieguez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Spain F4 | R32 | clay | Gabriel Trujillo Soler | 3-6 6-3 6-0 |
| 1999-05-07 | Spain 5 Masters 1 | R16 | clay | Oscar Martinez Dieguez | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.