Diego Hipperdinger defeated Mario Munoz Bejarano 2-6 7-5 6-4 in the Spain F21 round of 32 on clay. The upset overturned the form book — Mario Munoz Bejarano came in leading the head-to-head 2–1. Diego Hipperdinger narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-01-22 | France F3 | R32 | clay | Mario Munoz Bejarano | 7-6(1) 6-2 |
| 2000-09-11 | Romania F2 | F | clay | Diego Hipperdinger | 6-0 6-2 |
| 1999-10-15 | Spain 7 Masters 1 | R32 | clay | Mario Munoz Bejarano | 6-3 7-5 |