Dominique Monami defeated Anna Kournikova 6-3 6-1 in the Zurich round of 32 on hard. The result followed the form book — Dominique Monami came in leading the head-to-head 1–0, defending last year's round of 16. Dominique Monami extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-11 | Sydney | R16 | hard | Dominique Monami | 6-1 6-2 |