Kristie Boogert defeated Barbara Schwartz 6-1 6-2 in the Madrid round of 32 on clay. The upset overturned the form book — Barbara Schwartz came in leading the head-to-head 1–0, but Kristie Boogert had been the form player, winning 1 of their last 5 on clay. Kristie Boogert claimed a first win over Barbara Schwartz in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R64 | clay | Barbara Schwartz | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.