Ruxandra Dragomir Ilie defeated Jana Novotna 7-6 6-2 in the Berlin round of 32 on grass. The upset overturned the form book — Jana Novotna came in leading the head-to-head 2–1, defending last year's semi-final. Ruxandra Dragomir Ilie narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-23 | New Haven | R16 | hard | Ruxandra Dragomir Ilie | 7-6 6-0 |
| 1999-02-15 | Hanover | R16 | carpet | Jana Novotna | 6-3 6-3 |
| 1997-02-17 | Hanover | R16 | carpet | Jana Novotna | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.