Diego Hipperdinger defeated David Caballero 5-4 4-2 4-2 in the Spain F8 semi-final on clay. Diego Hipperdinger extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-16 | Spain 6 2 | QF | clay | Diego Hipperdinger | 7-5 4-6 7-6(3) |
| 1998-01-03 | Spain 1 Masters 1 | R32 | clay | David Caballero | 6-3 3-6 6-4 |