Luke Smith defeated Andrew Derer 7-6 7-5 in the Australia 2 4 round of 16 on hard. The upset overturned the form book — Andrew Derer came in leading the head-to-head 2–1. Luke Smith narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-11-24 | Australia F6 | R16 | grass | Andrew Derer | 6-3 7-5 |
| 2003-11-10 | Australia F4 | R32 | clay | Andrew Derer | 6-0 6-3 |
| 2002-01-28 | Australia 1 4 | QF | hard | Luke Smith | 6-3 5-7 7-6(5) |