Arantxa Sanchez Vicario defeated Sylvia Plischke 7-5 6-2 in the Wimbledon round of 32 on grass. The result followed the form book — Arantxa Sanchez Vicario came in defending last year's semi-final. Arantxa Sanchez Vicario extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | QF | clay | Arantxa Sanchez Vicario | 6-2 6-4 |
| 1999-05-03 | Rome | R16 | clay | Sylvia Plischke | 6-4 6-1 |