Rodrigo Guidolin defeated Juan Pablo Villar 6-3 7-5 in the Brazil F30 qualifying round on clay. The upset overturned the form book — Juan Pablo Villar came in leading the head-to-head 1–0, but Rodrigo Guidolin had been the form player, winning 6 of their last 10 on clay. Rodrigo Guidolin claimed a first win over Juan Pablo Villar in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-11-17 | Brazil F29 | QF | clay | Juan Pablo Villar | 2-6 6-1 6-4 |