Miriam Oremans defeated Magdalena Maleeva 6-4 7-5 in the Rosmalen round of 16 on grass. The upset overturned the form book — Magdalena Maleeva came in leading the head-to-head 3–1. Miriam Oremans narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-06-17 | s Hertogenbosch | R16 | grass | Magdalena Maleeva | 7-6 7-5 |
| 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 |
| 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.