Ekaterina Kozhokhina defeated Nadejda Ostrovskaya 6-3 6-3 in the Raanana 25K qualifying round on hard. The upset overturned the form book — Nadejda Ostrovskaya came in leading the head-to-head 1–0. Ekaterina Kozhokhina claimed a first win over Nadejda Ostrovskaya in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Minsk 10K | F | carpet | Nadejda Ostrovskaya | 7-5 6-1 |