Ai Sugiyama defeated Sabine Appelmans 6-3 7-6 in the Moscow round of 32 on hard. The upset overturned the form book — Sabine Appelmans came in leading the head-to-head 2–1. Ai Sugiyama narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-09 | Zurich | R32 | hard | Sabine Appelmans | 6-2 4-6 6-2 |
| 1999-05-03 | Rome | R64 | clay | Sabine Appelmans | 7-5 6-4 |
| 1996-12-30 | Hope Island | QF | hard | Ai Sugiyama | 6-2 3-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.