Mary Joe Fernandez defeated Anna Kournikova 6-7 6-4 7-6 in the Berlin round of 64 on grass. The upset overturned the form book — Anna Kournikova came in defending last year's semi-final. 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 |
| 1997-05-12 | Berlin | QF | grass | Mary Joe Fernandez | 6-1 6-4 |