Federico Cavallero defeated Guillermo Duran 6-3 6-2 in the Bolivia F2 round of 16 on clay. The upset overturned the form book — Guillermo Duran came in leading the head-to-head 1–0, but Federico Cavallero had been the form player, winning 6 of their last 10 on clay. Federico Cavallero claimed a first win over Guillermo Duran in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-22 | Argentina F10 | R32 | clay | Guillermo Duran | 6-2 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.