Jaslyn Hewitt defeated Lisa Mcshea 6-3 7-5 in the Bendigo 25K round of 32 on hard. The upset overturned the form book — Lisa Mcshea came in leading the head-to-head 1–0, but Jaslyn Hewitt had been the form player, winning 3 of their last 8 on hard. Jaslyn Hewitt claimed a first win over Lisa Mcshea in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Mount Gambier 25K | R32 | hard | Lisa Mcshea | 6-2 6-2 |