Yuri Radomsky defeated Rodrigo Guidolin 2-6 6-0 6-2 in the Brazil F29 round of 16 on clay. The upset overturned the form book — Rodrigo Guidolin came in leading the head-to-head 1–0. Yuri Radomsky claimed a first win over Rodrigo Guidolin in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-10-26 | Brazil F25 | R16 | clay | Rodrigo Guidolin | 6-2 6-3 |