Anna Kournikova defeated Magdalena Maleeva 6-4 7-5 in the Leipzig quarter-final on carpet. The upset overturned the form book — Magdalena Maleeva came in leading the head-to-head 1–0, defending last year's round of 32. Anna Kournikova claimed a first win over Magdalena Maleeva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-09-23 | Luxembourg | SF | hard | Magdalena Maleeva | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.