Anne Gaelle Sidot defeated Dominique Monami 3-6 6-2 6-3 in the Leipzig round of 16 on carpet. The upset overturned the form book — Dominique Monami came in leading the head-to-head 1–0, defending last year's semi-final. Anne Gaelle Sidot claimed a first win over Dominique Monami in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Luxembourg | R16 | hard | Dominique Monami | 4-6 6-4 6-4 |