Magdalena Maleeva defeated Ai Sugiyama 6-1 6-1 in the Tokyo quarter-final on hard. The upset overturned the form book — Ai Sugiyama came in leading the head-to-head 7–1, defending last year's round of 16. Magdalena Maleeva narrowed the head-to-head to 7–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-09 | Rome | R64 | clay | Ai Sugiyama | 6-2 6-4 |
| 2004-01-05 | Gold Coast | QF | hard | Ai Sugiyama | 4-6 7-6(4) 6-3 |
| 2003-08-04 | Los Angeles | QF | hard | Ai Sugiyama | 6-2 4-6 6-2 |
| 2003-03-05 | Indian Wells | R32 | hard | Ai Sugiyama | 6-4 6-3 |
| 2002-05-13 | Rome | R32 | clay | Ai Sugiyama | 7-6(3) 7-5 |
| 2001-10-22 | Linz | R16 | hard | Magdalena Maleeva | 1-6 6-3 6-1 |
| 2000-01-17 | Australian Open | R128 | hard | Ai Sugiyama | 7-6(3) 7-6(4) |
| 1998-01-04 | Hope Island | R32 | hard | Ai Sugiyama | 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 (21 vs 160). ATP, WTA & Challenger.