Magdalena Maleeva defeated Karina Habsudova 6-3 6-3 in the Canadian Open round of 64 on hard. The upset overturned the form book — Karina Habsudova came in leading the head-to-head 2–1. Magdalena Maleeva narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-10-27 | Kremlin Cup | R32 | carpet | Karina Habsudova | 6-1 6-3 |
| 1997-08-25 | US Open | R32 | hard | Karina Habsudova | 0-6 7-5 6-1 |
| 1997-02-17 | Hanover | R16 | carpet | Magdalena Maleeva | 0-6 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.