Kimberly Po Messerli defeated Kristie Boogert 6-4 6-2 in the Oklahoma round of 32 on hard. The upset overturned the form book — Kristie Boogert came in leading the head-to-head 1–0, defending last year's round of 32. Kimberly Po Messerli claimed a first win over Kristie Boogert in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-05-18 | Madrid | R16 | clay | Kristie Boogert | 4-6 6-0 6-2 |