Ai Sugiyama defeated Arantxa Sanchez Vicario 6-1 7-6 in the Kremlin Cup quarter-final on carpet. The upset overturned the form book — Arantxa Sanchez Vicario came in leading the head-to-head 7–0. Ai Sugiyama claimed a first win over Arantxa Sanchez Vicario in eight meetings, narrowing the head-to-head to 7–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-08-27 | US Open | R64 | hard | Arantxa Sanchez Vicario | 6-3 6-2 |
| 2001-05-07 | Berlin | R32 | grass | Arantxa Sanchez Vicario | 6-3 6-3 |
| 1998-08-10 | Manhattan Beach | R16 | hard | Arantxa Sanchez Vicario | 4-6 6-4 6-4 |
| 1998-01-19 | Australian Open | R16 | hard | Arantxa Sanchez Vicario | 6-2 6-4 |
| 1997-11-10 | Philadelphia | R16 | carpet | Arantxa Sanchez Vicario | 6-1 7-6 |
| 1997-08-04 | Manhattan Beach | R16 | hard | Arantxa Sanchez Vicario | 6-3 7-5 |
| 1997-05-26 | Roland Garros | R64 | clay | Arantxa Sanchez Vicario | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.