Anabel Medina Garrigues defeated Ai Sugiyama 6-2 4-6 6-4 in the Rome round of 32 on clay. The upset overturned the form book — Ai Sugiyama came in leading the head-to-head 3–0, defending last year's round of 16. Anabel Medina Garrigues claimed a first win over Ai Sugiyama in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-01-12 | Sydney | R16 | hard | Ai Sugiyama | 2-6 6-1 6-2 |
| 2008-03-24 | Miami | R64 | hard | Ai Sugiyama | 6-2 6-3 |
| 2006-08-14 | Montreal | R32 | hard | Ai Sugiyama | 6-4 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 (200 vs 141). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About