Jana Kandarr defeated Ai Sugiyama 1-6 7-5 7-5 in the Oklahoma City round of 32 on carpet. The upset overturned the form book — Ai Sugiyama came in leading the head-to-head 2–0. Jana Kandarr claimed a first win over Ai Sugiyama in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | New Haven | R32 | hard | Ai Sugiyama | 6-4 6-4 |
| 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.