Aleksandra Filipovski defeated Karolina Jovanovic 6-4 5-7 7-6 in the Prokuplje 10K round of 32 on clay. The upset overturned the form book — Karolina Jovanovic came in leading the head-to-head 1–0, but Aleksandra Filipovski had been the form player, winning 6 of their last 10 on clay. Aleksandra Filipovski claimed a first win over Karolina Jovanovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-29 | Prokuplje 10K | SF | clay | Karolina Jovanovic | 6-2 3-6 6-4 |