Jana Kandarr defeated Magdalena Maleeva 6-3 7-5 in the Estoril round of 16 on clay. The upset overturned the form book — Magdalena Maleeva came in leading the head-to-head 2–0. Jana Kandarr claimed a first win over Magdalena Maleeva in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-30 | Leipzig | R32 | carpet | Magdalena Maleeva | 6-2 6-2 |
| 1999-11-29 | Cergy Pontoise 50K | SF | hard | Magdalena Maleeva | 6-0 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.