Mary Joe Fernandez defeated Anna Kournikova 6-1 6-4 in the Berlin quarter-final on grass. Mary Joe Fernandez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Stanford | R16 | hard | Anna Kournikova | 6-4 6-4 |
| 1999-05-10 | Berlin | R64 | grass | Mary Joe Fernandez | 6-7 6-4 7-6 |