Cristhian Ignacio Benedetti defeated Nicolas Santos 4-6 6-3 7-5 in the Brazil F7 qualifying round on clay. The upset overturned the form book — Nicolas Santos came in leading the head-to-head 2–0. Cristhian Ignacio Benedetti claimed a first win over Nicolas Santos in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-25 | Brazil F4 | R16 | clay | Nicolas Santos | 6-0 4-6 6-1 |
| 2007-09-24 | Brazil F15 | R16 | clay | Nicolas Santos | 1-6 6-3 7-6(5) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.