Magdalena Maleeva defeated Sabine Appelmans 6-1 1-6 6-3 in the Sydney round of 32 on hard. The upset overturned the form book — Sabine Appelmans came in leading the head-to-head 2–1, defending last year's round of 16. Magdalena Maleeva narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Filderstadt | R32 | hard | Magdalena Maleeva | 6-4 5-7 7-5 |
| 1998-02-18 | Hanover | R16 | carpet | Sabine Appelmans | 7-5 6-3 |
| 1997-02-10 | Paris | R32 | carpet | Sabine Appelmans | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.