Andrew Derer defeated Jaymon Crabb 6-3 6-3 in the Sydney q32 on hard. The upset overturned the form book — Jaymon Crabb came in leading the head-to-head 2–1. Andrew Derer narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-02-14 | Australia F1 | R16 | hard | Andrew Derer | 7-6(5) 7-5 |
| 2005-01-13 | Australian Open | Q128 | hard | Jaymon Crabb | 1-0 |
| 2003-11-03 | Australia F3 | R32 | clay | Jaymon Crabb | 6-7(2) 7-5 6-1 |