Cristhian Ignacio Benedetti defeated Carlos Oliveira 7-6 6-3 in the Brazil F13 round of 16 on clay. The upset overturned the form book — Carlos Oliveira came in leading the head-to-head 1–0. Cristhian Ignacio Benedetti claimed a first win over Carlos Oliveira in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-01 | Brazil F5 | QF | clay | Carlos Oliveira | 6-3 6-2 |