Ai Sugiyama defeated Jane Chi 7-6 6-3 in the Tokyo semi-final on hard. The result followed the form book — Ai Sugiyama came in leading the head-to-head 1–0, defending the title. Ai Sugiyama extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Tokyo | R16 | hard | Ai Sugiyama | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.