Ai Sugiyama defeated Dominique Monami 6-2 4-6 6-3 in the Kremlin Cup semi-final on carpet. The upset overturned the form book — Dominique Monami came in leading the head-to-head 3–0. Ai Sugiyama claimed a first win over Dominique Monami in four meetings, narrowing 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) |
| 1999-10-11 | Zurich | R32 | hard | Dominique Monami | 3-6 6-4 6-2 |
| 1999-08-02 | San Diego | R16 | hard | Dominique Monami | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.