Iroda Tulyaganova defeated Nadejda Ostrovskaya 6-3 7-5 in the Tashkent round of 16 on hard. The upset overturned the form book — Nadejda Ostrovskaya came in leading the head-to-head 2–0, defending last year's round of 16. Iroda Tulyaganova claimed a first win over Nadejda Ostrovskaya in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-01 | Istanbul 10K | R16 | hard | Nadejda Ostrovskaya | 7-5 6-4 |
| 1998-03-25 | Ashkelon 10K | R32 | hard | Nadejda Ostrovskaya | 6-4 4-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.