Natalia Zvereva defeated Venus Williams 6-2 6-1 in the Eastbourne round of 16 on grass. The upset overturned the form book — Venus Williams came in leading the head-to-head 2–0, defending last year's round of 16. Natalia Zvereva claimed a first win over Venus Williams in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | San Diego | R16 | hard | Venus Williams | 7-5 6-1 |
| 1999-05-24 | Roland Garros | R64 | clay | Venus Williams | 7-6(3) 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.