Elena Voropaeva defeated Jana Macurova 2-6 6-4 6-2 in the Presov 10K round of 16 on clay. The upset overturned the form book — Jana Macurova came in leading the head-to-head 1–0. Elena Voropaeva claimed a first win over Jana Macurova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Minsk 10K | QF | carpet | Jana Macurova | 6-3 6-3 |