Holly Parkinson defeated Jana Nejedly 6-2 6-3 in the Hobart round of 32 on hard. The upset overturned the form book — Jana Nejedly came in leading the head-to-head 2–0. Holly Parkinson claimed a first win over Jana Nejedly in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-13 | Hopewell Junction 25K | SF | hard | Jana Nejedly | 3-6 6-4 6-4 |
| 1997-06-24 | Greenwood 10K | F | hard | Jana Nejedly | 7-5 6-3 |