Nadejda Ostrovskaya defeated Olga Vymetalkova 1-6 6-4 6-1 in the Ljubljana 25K qualifying round on carpet. The result followed the form book — Nadejda Ostrovskaya came in leading the head-to-head 1–0. Nadejda Ostrovskaya extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-08 | Rungsted 25K | R16 | carpet | Nadejda Ostrovskaya | 3-6 6-4 6-4 |