Anna Kournikova defeated Mary Joe Fernandez 6-4 6-4 in the Stanford round of 16 on hard. The upset overturned the form book — Mary Joe Fernandez came in leading the head-to-head 2–0, defending last year's round of 16. Anna Kournikova claimed a first win over Mary Joe Fernandez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Berlin | R64 | grass | Mary Joe Fernandez | 6-7 6-4 7-6 |
| 1997-05-12 | Berlin | QF | grass | Mary Joe Fernandez | 6-1 6-4 |