Julie Halard Decugis defeated Anke Huber 4-6 7-6 6-2 in the New Haven round of 32 on hard. The upset overturned the form book — Anke Huber came in leading the head-to-head 2–1, defending last year's quarter-final, but Julie Halard Decugis had been the form player, winning 4 of their last 6 on hard. Julie Halard Decugis 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 |
| 1999-10-04 | Filderstadt | R32 | hard | Anke Huber | 4-6 7-5 6-1 |