Nadejda Ostrovskaya defeated Angelika Roesch 3-6 6-4 6-4 in the Palermo round of 16 on clay. The upset overturned the form book — Angelika Roesch came in leading the head-to-head 2–1, but Nadejda Ostrovskaya had been the form player, winning 3 of their last 5 on clay. Nadejda Ostrovskaya narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-09-01 | Fano 50K | R32 | clay | Angelika Roesch | 2-6 7-5 7-6(5) |
| 1999-06-21 | Sopot 25K | R32 | clay | Angelika Roesch | 6-0 4-6 6-2 |
| 1997-07-16 | Torun 10K | R16 | clay | Nadejda Ostrovskaya | 4-6 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.