Chanda Rubin defeated Venus Williams 6-4 6-0 in the Amelia Island round of 32 on clay. The upset overturned the form book — Venus Williams came in leading the head-to-head 9–0. Chanda Rubin claimed a first win over Venus Williams in ten meetings, narrowing the head-to-head to 9–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-08-30 | US Open | R32 | hard | Venus Williams | 7-6(4) 6-3 |
| 2002-08-26 | US Open | R16 | hard | Venus Williams | 6-2 4-6 7-5 |
| 2002-05-27 | Roland Garros | R16 | clay | Venus Williams | 6-3 6-2 |
| 2000-10-14 | Linz | SF | hard | Venus Williams | 6-4 6-0 |
| 2000-05-15 | Rome | R32 | clay | Venus Williams | 6-1 6-2 |
| 1999-01-18 | Australian Open | R16 | hard | Venus Williams | 7-6(3) 6-4 |
| 1998-08-03 | San Diego | R16 | hard | Venus Williams | 6-3 6-2 |
| 1998-06-22 | Wimbledon | R32 | grass | Venus Williams | 6-3 6-4 |
| 1997-06-17 | Eastbourne | R32 | grass | Venus Williams | 6-4 6-4 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (22 vs 199). ATP, WTA & Challenger.