Nadejda Ostrovskaya defeated Tatiana Poutchek 3-6 6-1 7-6 in the Sopot q16 on clay. The upset overturned the form book — Tatiana Poutchek came in leading the head-to-head 4–2, defending last year's round of 32, but Nadejda Ostrovskaya had been the form player, winning 2 of their last 4 on clay. Nadejda Ostrovskaya narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-09-24 | Batumi 75K | F | carpet | Tatiana Poutchek | 7-5 4-6 6-3 |
| 2000-10-02 | Batumi 75K | F | clay | Tatiana Poutchek | 4-1 4-1 2-4 1-4 5-4(4) |
| 2000-03-06 | Ortisei 25K | F | hard | Nadejda Ostrovskaya | 4-6 6-1 7-6(6) |
| 2000-02-21 | Bushey 25K | R16 | carpet | Nadejda Ostrovskaya | 6-4 3-6 7-6(5) |
| 1999-05-03 | Beersheba 25K | SF | hard | Tatiana Poutchek | 6-7 6-4 6-2 |
| 1998-10-05 | Batumi 25K | R32 | carpet | Tatiana Poutchek | 6-0 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.