Leandro Ribeiro defeated Charles Costa 6-7 6-4 6-3 in the Brazil F9 round of 32 on clay. The upset overturned the form book — Charles Costa came in leading the head-to-head 1–0. Leandro Ribeiro claimed a first win over Charles Costa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-18 | Brazil F3 | R32 | clay | Charles Costa | 7-5 1-6 7-5 |