Ruxandra Dragomir Ilie defeated Magdalena Grzybowska 6-1 6-3 in the Palermo round of 32 on clay. The result followed the form book — Ruxandra Dragomir Ilie came in leading the head-to-head 3–1. Ruxandra Dragomir Ilie extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Canadian Open | R64 | hard | Ruxandra Dragomir Ilie | 6-4 7-5 |
| 1998-06-22 | Wimbledon | R128 | grass | Magdalena Grzybowska | 6-2 6-4 |
| 1998-01-04 | Hope Island | R16 | hard | Ruxandra Dragomir Ilie | 7-6 6-4 |
| 1997-07-14 | Prague | R32 | clay | Ruxandra Dragomir Ilie | 6-3 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.