Rodrigo Guidolin defeated Gustavo Junqueira De Andrade 7-6 4-6 6-3 in the Brazil F23 qualifying round on hard. The result followed the form book — Rodrigo Guidolin came in leading the head-to-head 2–1. Rodrigo Guidolin extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-15 | Brazil F7 | R32 | clay | Rodrigo Guidolin | 6-3 6-0 |
| 2009-05-18 | Brazil F3 | R32 | clay | Rodrigo Guidolin | 6-4 6-3 |
| 2008-08-11 | Brazil F15 | R32 | hard | Gustavo Junqueira De Andrade | 5-7 7-6(8) 2-0 |