Dessislava Mladenova defeated Tanya Germanlieva 5-7 6-4 6-3 in the Sofia 10K round of 32 on clay. The upset overturned the form book — Tanya Germanlieva came in leading the head-to-head 1–0, but Dessislava Mladenova had been the form player, winning 2 of their last 6 on clay. Dessislava Mladenova claimed a first win over Tanya Germanlieva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-21 | Sandanski 10K | R16 | clay | Tanya Germanlieva | 1-0 |