Rachel Mcquillan defeated Desislava Topalova 7-6 6-2 in the Mount Gambier Challenger semi-final on hard. The result followed the form book — Rachel Mcquillan came in leading the head-to-head 2–0. Rachel Mcquillan extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Nurioopta 25K | SF | hard | Rachel Mcquillan | 6-0 7-5 |
| 1999-11-15 | Mount Gambier 25K | R16 | hard | Rachel Mcquillan | 6-2 7-6 |