Ai Sugiyama advanced past Maria Sharapova via walkover in the Montreal round of 16. Ai Sugiyama claimed a first win over Maria Sharapova in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-07-27 | Stanford | R32 | hard | Maria Sharapova | 6-4 6-7(6) 6-1 |
| 2007-06-25 | Wimbledon | R32 | grass | Maria Sharapova | 6-3 6-3 |
| 2007-01-29 | Tokyo | QF | hard | Maria Sharapova | 4-6 6-0 6-1 |
| 2004-06-21 | Wimbledon | QF | grass | Maria Sharapova | 5-7 7-5 6-1 |
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 (68 vs 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About