Conchita Martinez defeated Ai Sugiyama 6-2 7-5 in the Sarasota round of 32 on clay. The result followed the form book — Conchita Martinez came in leading the head-to-head 2–1, defending last year's round of 32. Conchita Martinez extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 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 |
| 1998-01-11 | Sydney | R16 | hard | Ai Sugiyama | 7-6 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 (18 vs 172). ATP, WTA & Challenger.