Rodrigo Guidolin defeated Leonardo Kirche 6-4 3-6 6-3 in the Brazil F23 round of 16 on clay. The upset overturned the form book — Leonardo Kirche came in leading the head-to-head 5–3, but Rodrigo Guidolin had been the form player, winning 6 of their last 10 on clay. Rodrigo Guidolin narrowed the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-05-24 | Brazil F8 | F | clay | Leonardo Kirche | 4-6 6-3 7-6(4) |
| 2009-06-15 | Brazil F7 | QF | clay | Leonardo Kirche | 6-4 7-6(6) |
| 2009-05-04 | Brazil F1 | R32 | clay | Leonardo Kirche | 6-1 6-1 |
| 2008-05-05 | Brazil F3 | R16 | clay | Leonardo Kirche | 6-4 6-0 |
| 2007-09-17 | Brazil F14 | R32 | clay | Rodrigo Guidolin | 6-4 6-4 |
| 2005-05-09 | Brazil F3 | R16 | clay | Rodrigo Guidolin | 3-6 6-1 6-3 |
| 2005-04-18 | Chile F3 | R16 | clay | Rodrigo Guidolin | 6-7(4) 6-4 7-5 |
| 2003-08-11 | Brazil F3 | R32 | clay | Leonardo Kirche | 6-4 6-1 |