Ivaylo Traykov defeated Vladimir Obradovic 6-2 7-6 in the Bulgaria 1 3 round of 32 on clay. The upset overturned the form book — Vladimir Obradovic came in leading the head-to-head 1–0. Ivaylo Traykov claimed a first win over Vladimir Obradovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-06-26 | Serbia & Montenegro F2 | R32 | clay | Vladimir Obradovic | 6-3 6-4 |