Ai Sugiyama defeated Jana Kandarr 6-4 6-4 in the New Haven round of 32 on hard. Ai Sugiyama extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-02-19 | Oklahoma City | R32 | carpet | Jana Kandarr | 1-6 7-5 7-5 |
| 1996-08-26 | US Open | R128 | hard | Ai Sugiyama | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.