Ai Sugiyama defeated Flavia Pennetta 7-6 2-6 6-2 in the Wimbledon round of 64 on grass. Ai Sugiyama extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-21 | Los Angeles | R16 | hard | Flavia Pennetta | 7-6(5) 6-3 |
| 2004-10-18 | Zurich | R16 | hard | Ai Sugiyama | 7-6(1) 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 (67 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About