Ai Sugiyama defeated Karina Habsudova 6-2 4-6 7-5 in the US Open round of 64 on hard. Ai Sugiyama extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-05-11 | Berlin | R64 | grass | Ai Sugiyama | 6-0 6-2 |
| 1997-08-25 | US Open | R64 | hard | Karina Habsudova | 5-7 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.