Vladimir Obradovic defeated Timothy Neilly 6-4 3-6 6-2 in the USA F9 semi-final on clay. The upset overturned the form book — Timothy Neilly came in leading the head-to-head 1–0. Vladimir Obradovic claimed a first win over Timothy Neilly in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-04-27 | USA F9 | QF | clay | Timothy Neilly | 6-3 6-3 |