Conchita Martinez advanced past Serena Williams via walkover in the Charleston round of 16. Conchita Martinez claimed a first win over Serena Williams in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-12 | Rome | QF | clay | Serena Williams | 7-5 6-2 |
| 2003-04-07 | Charleston | R16 | clay | Serena Williams | 6-2 6-2 |
| 2000-08-07 | Los Angeles | QF | hard | Serena Williams | 6-2 4-6 6-2 |
| 1999-08-30 | US Open | R16 | hard | Serena Williams | 4-6 6-2 6-2 |
| 1998-05-04 | Rome | R16 | clay | Serena Williams | 6-2 6-2 |
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 (8 vs 199). ATP, WTA & Challenger.