Federico Dondo defeated Diego Hipperdinger 6-1 7-6 in the Chile F5 qualifying round on clay. The upset overturned the form book — Diego Hipperdinger came in leading the head-to-head 2–0. Federico Dondo claimed a first win over Diego Hipperdinger in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-16 | France F10 | R32 | clay | Diego Hipperdinger | 6-2 6-1 |
| 2000-05-15 | Argentina F5 | QF | clay | Diego Hipperdinger | 6-1 7-6(5) |