Ruxandra Dragomir Ilie defeated Jana Novotna 7-6 6-0 in the New Haven round of 16 on hard. The upset overturned the form book — Jana Novotna came in leading the head-to-head 2–1, defending last year's final. Ruxandra Dragomir Ilie narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Berlin | R32 | grass | Ruxandra Dragomir Ilie | 7-6 6-2 |
| 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.