Jana Novotna defeated Sylvia Plischke 6-3 6-1 in the Wimbledon round of 64 on grass. The upset overturned the form book — Sylvia Plischke came in leading the head-to-head 1–0, defending last year's round of 32. Jana Novotna claimed a first win over Sylvia Plischke in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R16 | clay | Sylvia Plischke | 6-3 7-6(5) |