Seiko Okamoto defeated Chiaki Nakajima 6-4 3-6 6-3 in the Kugayama 4 10K round of 32 on hard. The result followed the form book — Seiko Okamoto came in leading the head-to-head 1–0, defending last year's quarter-final. Seiko Okamoto extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Haibara 10K | R32 | carpet | Seiko Okamoto | 6-2 7-5 |