Dominique Monami defeated Venus Williams 6-1 6-2 in the Filderstadt round of 16 on hard. The upset overturned the form book — Venus Williams came in leading the head-to-head 2–0, but Dominique Monami had been the form player, winning 5 of their last 8 on hard. Dominique Monami claimed a first win over Venus Williams in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Rome | QF | clay | Venus Williams | 7-6 6-2 |
| 1998-03-05 | Indian Wells | R16 | hard | Venus Williams | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.