Oscar Serrano defeated David Caballero 6-3 6-3 in the Spain 1 3 round of 32 on clay. The upset overturned the form book — David Caballero came in leading the head-to-head 3–1, but Oscar Serrano had been the form player, winning 5 of their last 10 on clay. Oscar Serrano narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-01-30 | Spain 2 Masters 2 | F | clay | David Caballero | 6-3 6-2 |
| 1996-03-01 | Spain 3 Masters 1 | R32 | clay | Oscar Serrano | 6-0 6-4 |
| 1995-08-11 | Spain 7 Masters 4 | R16 | clay | David Caballero | 6-3 6-4 |
| 1995-05-12 | Spain 4 Masters 4 | R32 | clay | David Caballero | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.