Ai Sugiyama advanced when Katarina Srebotnik retired 7-6 4-6 5-1 in the Eastbourne round of 32. Ai Sugiyama extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-04-11 | Charleston | R16 | clay | Katarina Srebotnik | 6-1 4-6 6-1 |
| 2002-07-29 | San Diego | R16 | hard | Ai Sugiyama | 6-4 7-6(4) |
| 2001-10-01 | Japan Open | R16 | hard | Ai Sugiyama | 6-2 3-6 6-1 |
| 2000-01-31 | Tokyo | R32 | hard | Katarina Srebotnik | 6-3 6-3 |
| 1999-07-22 | Fed Cup WG2 RRA: JPN vs SLO | RR | hard | Ai Sugiyama | 6-1 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 (141 vs 162). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About