Vladimir Obradovic defeated Stefano Ianni 6-0 4-6 6-3 in the USA F6 round of 16 on hard. The upset overturned the form book — Stefano Ianni came in leading the head-to-head 2–0. Vladimir Obradovic claimed a first win over Stefano Ianni in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-05-03 | USA F11 | R16 | clay | Stefano Ianni | 6-3 7-5 |
| 2007-05-07 | USA F10 | QF | clay | Stefano Ianni | 6-4 6-4 |