Steffi Graf defeated Ai Sugiyama 6-4 6-3 in the Leipzig round of 16 on carpet. The result followed the form book — Steffi Graf came in leading the head-to-head 3–1. Steffi Graf extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-05 | Indian Wells | R16 | hard | Steffi Graf | 6-0 6-1 |
| 1999-01-11 | Sydney | R32 | hard | Steffi Graf | 6-0 6-4 |
| 1998-08-03 | San Diego | R16 | hard | Ai Sugiyama | 6-4 1-6 7-5 |
| 1998-03-05 | Indian Wells | R16 | hard | Steffi Graf | 6-0 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.