Dominique Monami defeated Magdalena Maleeva 7-6 6-4 in the New Haven round of 32 on hard. The upset overturned the form book — Magdalena Maleeva came in leading the head-to-head 1–0, but Dominique Monami had been the form player, winning 5 of their last 8 on hard. Dominique Monami claimed a first win over Magdalena Maleeva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-09 | Zurich | R32 | hard | Magdalena Maleeva | 6-7(5) 6-2 7-6(4) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.