Juan Pablo Brzezicki defeated Diego Hipperdinger 6-3 6-1 in the Spain F15 qualifying round on clay. The upset overturned the form book — Diego Hipperdinger came in leading the head-to-head 2–1. Juan Pablo Brzezicki narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-12 | Argentina 4 | R32 | clay | Juan Pablo Brzezicki | 3-2 |
| 2000-05-22 | Argentina F6 | F | clay | Diego Hipperdinger | 6-3 6-1 |
| 2000-05-08 | Argentina F4 | QF | clay | Diego Hipperdinger | 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.