Alexandra Stevenson defeated Maureen Drake 6-3 6-3 in the Toronto 50K qualifying round on hard. The result followed the form book — Alexandra Stevenson came in leading the head-to-head 1–0. Alexandra Stevenson extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Quebec City | R32 | hard | Alexandra Stevenson | 4-6 7-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.