Cristhian Ignacio Benedetti defeated Rodrigo Guidolin 7-5 6-4 in the Brazil F20 qualifying round on clay. The upset overturned the form book — Rodrigo Guidolin came in leading the head-to-head 5–0. Cristhian Ignacio Benedetti claimed a first win over Rodrigo Guidolin in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-10-25 | Brazil F30 | SF | clay | Rodrigo Guidolin | 6-3 6-2 |
| 2010-05-24 | Brazil F8 | QF | clay | Rodrigo Guidolin | 6-0 6-2 |
| 2009-06-22 | Brazil F8 | SF | clay | Rodrigo Guidolin | 6-4 6-4 |
| 2008-06-23 | Brazil F10 Teresina PL | F | clay | Rodrigo Guidolin | 7-6(5) 6-3 |
| 2008-06-16 | Brazil F9 | QF | hard | Rodrigo Guidolin | 6-2 6-2 |