Fernando Romboli defeated Carlos Oliveira 6-3 6-1 in the Brazil F4 round of 16 on clay. The upset overturned the form book — Carlos Oliveira came in leading the head-to-head 3–0. Fernando Romboli claimed a first win over Carlos Oliveira in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-17 | Brazil F15 | QF | clay | Carlos Oliveira | 6-2 7-5 |
| 2009-05-11 | Brazil F2 | QF | hard | Carlos Oliveira | 5-7 6-3 7-6(4) |
| 2008-10-06 | Brazil F23 | QF | clay | Carlos Oliveira | 6-0 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.