Sabine Appelmans defeated Ai Sugiyama 7-5 6-4 in the Rome round of 64 on clay. The upset overturned the form book — Ai Sugiyama came in leading the head-to-head 2–1, defending last year's round of 64. Sabine Appelmans narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-21 | Moscow | R32 | hard | Ai Sugiyama | 6-3 7-6(5) |
| 2000-10-09 | Zurich | R32 | hard | Sabine Appelmans | 6-2 4-6 6-2 |
| 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.