Rodrigo Guidolin defeated Fernando Romboli 6-3 2-6 6-3 in the Brazil F21 round of 16 on clay. The upset overturned the form book — Fernando Romboli came in leading the head-to-head 5–2, but Rodrigo Guidolin had been the form player, winning 5 of their last 9 on clay. Rodrigo Guidolin narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-07-19 | Brazil F16 | QF | clay | Fernando Romboli | 6-3 6-4 |
| 2010-07-12 | Brazil F15 | QF | clay | Rodrigo Guidolin | 6-2 6-2 |
| 2009-06-22 | Brazil F8 | F | clay | Fernando Romboli | 6-7(3) 7-6(4) |
| 2009-05-25 | Brazil F4 | SF | clay | Fernando Romboli | 6-7(4) 6-2 6-2 |
| 2008-10-13 | Brazil F24 | R16 | clay | Fernando Romboli | 6-2 6-2 |
| 2008-05-26 | Brazil F6 | QF | clay | Rodrigo Guidolin | 7-6(1) 6-2 |
| 2007-10-01 | Brazil F16 | R32 | clay | Fernando Romboli | 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.