Holly Parkinson defeated Diana Ospina 1-6 6-4 6-4 in the Kirkland 75K round of 32 on hard. The result followed the form book — Holly Parkinson came in leading the head-to-head 1–0. Holly Parkinson extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-06 | Mexico City 25K | R16 | hard | Holly Parkinson | 6-3 7-6 |