Gabriela Chmelinova defeated Jana Macurova 2-6 7-5 6-0 in the Cavtat 10K round of 32 on clay. The upset overturned the form book — Jana Macurova came in leading the head-to-head 2–0. Gabriela Chmelinova claimed a first win over Jana Macurova in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-09-30 | Trencianske Teplice 10K | R32 | clay | Jana Macurova | 6-4 6-0 |
| 1998-08-26 | Plzen 10K | QF | clay | Jana Macurova | 7-5 6-0 |