Maureen Drake defeated Anne Kremer 6-4 7-5 in the Quebec City round of 32 on hard. The upset overturned the form book — Anne Kremer came in defending last year's semi-final. Maureen Drake extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Canadian Open | R64 | hard | Maureen Drake | 6-2 6-3 |
| 1999-05-24 | Roland Garros | R128 | clay | Anne Kremer | 6-2 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (5 vs 41). ATP, WTA & Challenger.