Ai Sugiyama defeated Kimberly Po Messerli 6-3 6-1 in the Eastbourne round of 16 on grass. The upset overturned the form book — Kimberly Po Messerli 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 |
|---|---|---|---|---|---|
| 1997-07-21 | Stanford | R16 | hard | Kimberly Po Messerli | 6-3 6-1 |
| 1997-04-14 | Tokyo | SF | hard | Ai Sugiyama | 5-7 6-4 6-1 |
| 1997-01-13 | Australian Open | R64 | hard | Kimberly Po Messerli | 6-0 4-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.