Katarina Srebotnik defeated Ai Sugiyama 6-1 4-6 6-1 in the Charleston round of 16 on clay. The upset overturned the form book — Ai Sugiyama came in leading the head-to-head 4–1. Katarina Srebotnik narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-06-19 | Eastbourne | R32 | grass | Ai Sugiyama | 7-6(5) 4-6 5-1 RET |
| 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 (169 vs 149). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About