Irina Spirlea defeated Sabine Appelmans 6-3 6-1 in the Luxembourg round of 16 on hard. The upset overturned the form book — Sabine Appelmans came in leading the head-to-head 3–1, defending last year's quarter-final. Irina Spirlea narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Luxembourg | R32 | hard | Sabine Appelmans | 7-5 7-6 |
| 1998-02-18 | Hanover | R32 | carpet | Sabine Appelmans | 4-1 RET |
| 1997-05-12 | Berlin | R16 | grass | Sabine Appelmans | 7-6 2-6 6-3 |
| 1997-03-20 | Key Biscayne | R32 | hard | Irina Spirlea | 2-6 6-2 6-3 |