Ai Sugiyama defeated Magdalena Grzybowska 7-6 1-6 6-4 in the Australian Open round of 32 on hard. The result followed the form book — Ai Sugiyama came in leading the head-to-head 2–0, defending last year's round of 64. Ai Sugiyama extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R128 | grass | Ai Sugiyama | 6-1 6-2 |
| 1998-06-15 | Eastbourne | R32 | grass | Ai Sugiyama | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.