Ai Sugiyama defeated Magdalena Maleeva 6-2 6-4 in the Rome round of 64 on clay. The result followed the form book — Ai Sugiyama came in leading the head-to-head 6–2, defending last year's round of 16. Ai Sugiyama extended the head-to-head to 7–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-02-03 | Tokyo | QF | hard | Magdalena Maleeva | 6-1 6-1 |
| 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 (149 vs 11). ATP, WTA & Challenger.