Ai Sugiyama defeated Sabine Appelmans 6-3 7-6 in the Moscow round of 32 on hard. Ai Sugiyama extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-09 | Zurich | R32 | hard | Sabine Appelmans | 6-4 2-6 6-2 |
| 1999-05-03 | Rome | R64 | clay | Sabine Appelmans | 7-5 6-4 |
| 1997-01-01 | Gold Coast | QF | hard | Ai Sugiyama | 6-2 3-6 7-6(0) |
| 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.