Carlos Oliveira defeated Cristhian Ignacio Benedetti 6-3 6-2 in the Brazil F5 qualifying round on clay. The upset overturned the form book — Cristhian Ignacio Benedetti came in leading the head-to-head 1–0. Carlos Oliveira claimed a first win over Cristhian Ignacio Benedetti in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-28 | Brazil F13 | R16 | clay | Cristhian Ignacio Benedetti | 7-6(1) 6-3 |