Stephanie Halsell defeated Kylie Hunt 6-4 6-4 in the Williamsburg 10K round of 16 on hard. The upset overturned the form book — Kylie Hunt came in leading the head-to-head 1–0. Stephanie Halsell claimed a first win over Kylie Hunt in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Poza Rica 10K | QF | hard | Kylie Hunt | 6-3 3-6 7-6 |