Leonardo Kirche defeated Cristhian Ignacio Benedetti 6-2 6-4 in the Brazil F7 semi-final on clay. The upset overturned the form book — Cristhian Ignacio Benedetti came in leading the head-to-head 3–0, but Leonardo Kirche had been the form player, winning 4 of their last 8 on clay. Leonardo Kirche claimed a first win over Cristhian Ignacio Benedetti in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-08 | Brazil F6 | SF | clay | Cristhian Ignacio Benedetti | 6-1 7-6(6) |
| 2008-06-23 | Brazil F10 Teresina PL | SF | clay | Cristhian Ignacio Benedetti | 6-3 6-3 |
| 2008-06-02 | Brazil F7 | R32 | clay | Cristhian Ignacio Benedetti | 6-4 3-6 6-4 |