Tatiana Perebiynis defeated Nadejda Ostrovskaya 3-6 6-2 6-2 in the Redbridge 25K round of 32 on hard. The upset overturned the form book — Nadejda Ostrovskaya came in leading the head-to-head 2–0. Tatiana Perebiynis claimed a first win over Nadejda Ostrovskaya in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Batumi 75K | SF | clay | Nadejda Ostrovskaya | 5-4(5) 4-1 4-0 |
| 1999-02-01 | Istanbul 10K | F | hard | Nadejda Ostrovskaya | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.