Elena Gantcheva defeated Nadejda Vassileva 6-0 6-2 in the Ankara 10K round of 32 on clay. The upset overturned the form book — Nadejda Vassileva came in leading the head-to-head 1–0. Elena Gantcheva claimed a first win over Nadejda Vassileva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-09 | Sofia 10K | R32 | clay | Nadejda Vassileva | 4-1 4-0 3-5 5-3 |