Simeon Ivanov defeated Vasko Mladenov 6-7 6-3 6-2 in the Bulgaria F5 round of 16 on clay. The upset overturned the form book — Vasko Mladenov came in leading the head-to-head 3–0. Simeon Ivanov claimed a first win over Vasko Mladenov in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-08-27 | Bulgaria F6 | R32 | clay | Vasko Mladenov | 7-6(7) 6-4 |
| 2007-05-14 | Bulgaria F2 | R32 | clay | Vasko Mladenov | 6-3 6-4 |
| 2007-05-07 | Bulgaria F1 | R32 | clay | Vasko Mladenov | 7-5 4-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.