Anke Huber defeated Julie Halard Decugis 4-6 7-5 6-1 in the Filderstadt round of 32 on hard. The upset overturned the form book — Julie Halard Decugis came in leading the head-to-head 2–1. Anke Huber narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | WTA Tour Championships | R16 | carpet | Anke Huber | 6-1 6-2 |
| 1999-10-11 | Zurich | R16 | hard | Julie Halard Decugis | 6-2 6-4 |
| 1999-08-23 | New Haven | R32 | hard | Julie Halard Decugis | 4-6 7-6 6-2 |