Dejan Petrovic defeated Luke Smith 6-4 6-4 in the Australia 1 4 semi-final on hard. The result followed the form book — Dejan Petrovic came in leading the head-to-head 1–0. Dejan Petrovic extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Australia F4 | R16 | grass | Dejan Petrovic | 6-3 6-4 |