Ai Sugiyama defeated Anne Kremer 3-6 6-4 6-4 in the Charleston round of 64 on clay. The result followed the form book — Ai Sugiyama came in leading the head-to-head 1–0, defending last year's round of 64. Ai Sugiyama extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Kremlin Cup | R32 | carpet | Ai Sugiyama | 6-1 3-6 6-2 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (172 vs 41). ATP, WTA & Challenger.