Ruxandra Dragomir Ilie defeated Anna Kournikova 6-7 6-3 6-3 in the Hilton Head round of 16 on clay. Ruxandra Dragomir Ilie extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-05 | Amelia Island | SF | clay | Ruxandra Dragomir Ilie | 6-3 7-5 |
| 1998-08-17 | Canadian Open | R32 | hard | Anna Kournikova | 4-6 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.