Gabriel Pitta defeated Alexandre Simoni 6-3 6-2 in the Brazil F14 round of 16 on clay. The upset overturned the form book — Alexandre Simoni came in leading the head-to-head 3–0. Gabriel Pitta claimed a first win over Alexandre Simoni in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-09 | Brazil F14 | R32 | clay | Alexandre Simoni | 6-4 6-1 |
| 2005-09-19 | Brazil F11 | R32 | clay | Alexandre Simoni | 6-4 7-6(3) |
| 2005-08-15 | Brazil F6 | F | hard | Alexandre Simoni | 6-3 6-2 |