Ai Sugiyama defeated Jana Novotna 5-7 6-2 6-1 in the Canadian Open round of 32 on hard. The upset overturned the form book — Jana Novotna came in leading the head-to-head 3–0, defending last year's semi-final. Ai Sugiyama claimed a first win over Jana Novotna in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-10-27 | Kremlin Cup | F | carpet | Jana Novotna | 6-3 6-4 |
| 1997-10-12 | Zurich | R16 | hard | Jana Novotna | 6-0 6-7 6-2 |
| 1997-06-17 | Eastbourne | QF | grass | Jana Novotna | 6-2 6-7 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.