1. Round | 08/11/2008 | Canterbury United | - | YoungHeart Manawatu | 0:1 | ||||
4. Round | 29/11/2008 | Waitakere United | - | Canterbury United | 1:1 | ||||
6. Round | 14/12/2008 | Hawke’s Bay United FC | - | Canterbury United | 1:2 | ||||
7. Round | 21/12/2008 | Canterbury United | - | Auckland City FC | 2:1 | ||||
9. Round | 18/01/2009 | Canterbury United | - | Otago United | 1:2 | ||||
11. Round | 01/02/2009 | Canterbury United | - | Waitakere United | 0:2 | ||||
12. Round | 22/02/2009 | Team Wellington | - | Canterbury United | 3:1 |