Jaymon Crabb advanced when Andrew Derer retired 1-0 in the Australian Open q128. Jaymon Crabb 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 |
| 2005-01-07 | Sydney | Q32 | hard | Andrew Derer | 6-3 6-3 |
| 2003-11-03 | Australia F3 | R32 | clay | Jaymon Crabb | 6-7(2) 7-5 6-1 |