Dominique Monami defeated Ai Sugiyama 3-6 6-4 6-2 in the Zurich round of 32 on hard. The result followed the form book — Dominique Monami came in leading the head-to-head 2–1, defending last year's quarter-final. Dominique Monami extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-31 | San Diego | R32 | hard | Dominique Monami | 6-2 7-6(4) |
| 1999-08-02 | San Diego | R16 | hard | Dominique Monami | 6-2 6-4 |
| 1997-10-27 | Kremlin Cup | SF | carpet | Ai Sugiyama | 6-2 4-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.