Magdalena Maleeva defeated Miriam Oremans 7-6 7-5 in the s Hertogenbosch round of 16 on grass. The upset overturned the form book — Miriam Oremans came in defending last year's round of 16. Magdalena Maleeva extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-14 | Montreal | Q32 | hard | Magdalena Maleeva | 6-4 6-2 |
| 2000-06-26 | Wimbledon | R64 | grass | Miriam Oremans | 1-6 7-5 6-3 |
| 1997-06-16 | Rosmalen | R16 | grass | Miriam Oremans | 6-4 7-5 |
| 1996-05-27 | Roland Garros | R32 | clay | Magdalena Maleeva | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.