Jana Macurova defeated Adriana Jerabek 1-6 6-2 6-0 in the Hechinger 10K round of 16 on clay. The upset overturned the form book — Adriana Jerabek came in leading the head-to-head 1–0, but Jana Macurova had been the form player, winning 4 of their last 8 on clay. Jana Macurova claimed a first win over Adriana Jerabek in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Valasske Mezirici 10K | R32 | clay | Adriana Jerabek | 6-4 6-3 |