Izak Van Der Merwe defeated Vladimir Obradovic 6-1 6-3 in the USA F7 round of 16 on hard. The upset overturned the form book — Vladimir Obradovic came in leading the head-to-head 1–0. Izak Van Der Merwe claimed a first win over Vladimir Obradovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-03-03 | USA F6 | R32 | hard | Vladimir Obradovic | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.