David Caballero defeated Diego Hipperdinger 6-3 3-6 6-4 in the Spain 1 Masters 1 round of 32 on clay. The upset overturned the form book — Diego Hipperdinger came in leading the head-to-head 2–0. David Caballero claimed a first win over Diego Hipperdinger in three meetings, narrowing 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) |
| 2000-08-28 | Spain F8 | SF | clay | Diego Hipperdinger | 5-4(5) 4-2 4-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.