Andre Pinheiro defeated Nicolas Santos 3-6 6-2 7-6 in the Brazil F23 qualifying round on clay. The upset overturned the form book — Nicolas Santos came in leading the head-to-head 2–0. Andre Pinheiro claimed a first win over Nicolas Santos in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-11 | Brazil F2 | R16 | hard | Nicolas Santos | 6-1 6-1 |
| 2008-10-20 | Brazil F25 | R32 | clay | Nicolas Santos | 1-6 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.