Sylvia Plischke defeated Jana Novotna 6-3 7-6 in the Roland Garros round of 16 on clay. The upset overturned the form book — Jana Novotna came in leading the head-to-head 1–0, defending last year's quarter-final. Sylvia Plischke claimed a first win over Jana Novotna in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R64 | grass | Jana Novotna | 6-3 6-1 |