Juan Pablo Brzezicki defeated Emiliano Redondi 5-7 6-2 6-2 in the Bolivia F1 round of 16 on clay. The upset overturned the form book — Emiliano Redondi came in leading the head-to-head 1–0. Juan Pablo Brzezicki claimed a first win over Emiliano Redondi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-31 | Argentina 2 Masters 4 | R32 | clay | Emiliano Redondi | 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.