Sylvia Plischke defeated Anna Kournikova 6-2 4-6 6-3 in the Roland Garros round of 64 on clay. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 3–0, defending last year's round of 16. Sylvia Plischke claimed a first win over Anna Kournikova in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-02-28 | Scottsdale | R16 | hard | Anna Kournikova | 6-1 6-1 |
| 1998-02-23 | Linz | R32 | hard | Anna Kournikova | 5-7 6-4 7-5 |
| 1997-05-12 | Berlin | R64 | grass | Anna Kournikova | 6-2 6-2 |