Cristhian Ignacio Benedetti defeated Marcelo Demoliner 6-4 2-6 6-3 in the Brazil F32 qualifying round on clay. The upset overturned the form book — Marcelo Demoliner came in leading the head-to-head 2–0. Cristhian Ignacio Benedetti claimed a first win over Marcelo Demoliner in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-18 | Brazil F3 | QF | clay | Marcelo Demoliner | 6-3 6-2 |
| 2008-07-28 | Brazil F13 | SF | clay | Marcelo Demoliner | 6-1 7-6(3) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.