Yumiko Kitamura defeated Ayami Takase 6-3 6-4 in the Kugayama 2 10K round of 16 on hard. The upset overturned the form book — Ayami Takase came in leading the head-to-head 1–0, but Yumiko Kitamura had been the form player, winning 3 of their last 6 on hard. Yumiko Kitamura claimed a first win over Ayami Takase in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Haibara 10K | R32 | carpet | Ayami Takase | 6-1 0-6 7-5 |