Sylvia Plischke defeated Ai Sugiyama 6-4 6-7 6-3 in the Wimbledon round of 128 on grass. The upset overturned the form book — Ai Sugiyama came in leading the head-to-head 1–0, defending last year's round of 128. Sylvia Plischke claimed a first win over Ai Sugiyama in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Roland Garros | R32 | clay | Ai Sugiyama | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.