Dominique Monami defeated Anne Gaelle Sidot 4-6 6-4 6-4 in the Luxembourg round of 16 on hard. The upset overturned the form book — Anne Gaelle Sidot came in leading the head-to-head 1–0, defending last year's round of 32, but Dominique Monami had been the form player, winning 2 of their last 4 on hard. Dominique Monami claimed a first win over Anne Gaelle Sidot in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Leipzig | R16 | carpet | Anne Gaelle Sidot | 3-6 6-2 6-3 |