Ai Sugiyama defeated Dinara Safina 6-0 2-6 6-4 in the Rome round of 32 on clay. The upset overturned the form book — Dinara Safina came in leading the head-to-head 3–2. Ai Sugiyama narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-01-12 | Sydney | SF | hard | Dinara Safina | 6-4 7-6(3) |
| 2007-03-19 | Miami | R32 | hard | Dinara Safina | 6-4 3-6 6-1 |
| 2005-01-03 | Gold Coast | R32 | hard | Dinara Safina | 6-3 6-2 |
| 2003-09-15 | Shanghai | QF | hard | Ai Sugiyama | 6-4 7-6(7) |
| 2003-03-19 | Miami | R64 | hard | Ai Sugiyama | 3-6 7-5 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 (172 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About