Leonardo Kirche defeated Gabriel Pitta 6-3 6-4 in the Brazil F5 round of 32 on clay. The upset overturned the form book — Gabriel Pitta came in leading the head-to-head 2–1. Leonardo Kirche narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-09-24 | Brazil F15 | QF | clay | Gabriel Pitta | 6-4 7-6(4) |
| 2006-06-05 | Brazil F4 | R16 | clay | Gabriel Pitta | 6-4 7-5 |
| 2005-08-22 | Brazil F7 | R32 | clay | Leonardo Kirche | 7-5 2-6 7-5 |