Kristie Boogert defeated Kimberly Po Messerli 4-6 6-0 6-2 in the Madrid round of 16 on clay. The upset overturned the form book — Kimberly Po Messerli came in leading the head-to-head 1–0, defending last year's round of 32. Kristie Boogert claimed a first win over Kimberly Po Messerli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-22 | Oklahoma | R32 | hard | Kimberly Po Messerli | 6-4 6-2 |