Ai Sugiyama defeated Shi Ting Wang 6-3 6-2 in the Tokyo semi-final on hard. The result followed the form book — Ai Sugiyama came in leading the head-to-head 2–0, defending the title. Ai Sugiyama extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-02 | Tokyo | R32 | hard | Ai Sugiyama | 6-2 6-3 |
| 1998-01-04 | Hope Island | SF | hard | Ai Sugiyama | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.