Stefano Ianni defeated Vladimir Obradovic 6-3 7-5 in the USA F11 round of 16 on clay. Stefano Ianni extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-03-03 | USA F6 | R16 | hard | Vladimir Obradovic | 6-0 4-6 6-3 |
| 2007-05-07 | USA F10 | QF | clay | Stefano Ianni | 6-4 6-4 |