Anna Kournikova defeated Ruxandra Dragomir Ilie 4-6 6-2 6-4 in the Canadian Open round of 32 on hard. The upset overturned the form book — Ruxandra Dragomir Ilie came in leading the head-to-head 2–0, defending last year's round of 64. Anna Kournikova claimed a first win over Ruxandra Dragomir Ilie in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-17 | Hilton Head | R16 | clay | Ruxandra Dragomir Ilie | 6-7(2) 6-3 6-3 |
| 1999-04-05 | Amelia Island | SF | clay | Ruxandra Dragomir Ilie | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.