Ai Sugiyama defeated Conchita Martinez 7-6 6-3 in the Sydney round of 16 on hard. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 3–0. Ai Sugiyama claimed a first win over Conchita Martinez in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-03-31 | Sarasota | R32 | clay | Conchita Martinez | 6-2 7-5 |
| 2000-05-29 | Roland Garros | R16 | clay | Conchita Martinez | 5-7 6-3 6-4 |
| 1998-05-11 | Berlin | QF | grass | Conchita Martinez | 6-3 6-3 |
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 (172 vs 18). ATP, WTA & Challenger.