Karolina Jovanovic defeated Aleksandra Filipovski 6-2 3-6 6-4 in the Prokuplje 10K semi-final on clay. The upset overturned the form book — Aleksandra Filipovski came in leading the head-to-head 1–0. Karolina Jovanovic claimed a first win over Aleksandra Filipovski in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-07-06 | Prokuplje 10K | R32 | clay | Aleksandra Filipovski | 6-4 5-7 7-6(6) |