Magdalena Maleeva defeated Anke Huber 3-6 7-6 6-1 in the Tokyo round of 32 on hard. The upset overturned the form book — Anke Huber came in leading the head-to-head 3–2, defending last year's semi-final. Magdalena Maleeva narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-10-01 | Moscow | R32 | hard | Magdalena Maleeva | 6-3 7-5 |
| 2001-02-06 | Paris | SF | carpet | Anke Huber | 6-4 7-5 |
| 1999-07-05 | Portschach | R16 | clay | Anke Huber | 3-6 6-4 6-3 |
| 1999-06-14 | s Hertogenbosch | R16 | grass | Magdalena Maleeva | 6-1 6-2 |
| 1997-07-28 | San Diego | R32 | hard | Anke Huber | 7-5 1-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.