Vladimir Obradovic defeated Aleksandar Grubin 6-1 6-2 in the Serbia & Montenegro F5 round of 16 on clay. The upset overturned the form book — Aleksandar Grubin came in leading the head-to-head 2–0. Vladimir Obradovic claimed a first win over Aleksandar Grubin in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-06-25 | Serbia F2 | R32 | clay | Aleksandar Grubin | 6-4 5-7 7-5 |
| 2006-07-31 | Serbia & Montenegro F3 | R32 | clay | Aleksandar Grubin | 6-4 6-2 |