Sachie Umehara defeated Ayami Takase 6-2 6-4 in the Kugayama 4 10K round of 16 on hard. The upset overturned the form book — Ayami Takase came in leading the head-to-head 1–0. Sachie Umehara claimed a first win over Ayami Takase in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-06 | Ibaraki 1 10K | R32 | hard | Ayami Takase | 7-6 6-3 |