1. Round | 08/11/2008 | Canterbury United | - | YoungHeart Manawatu | 0:1 | ||||
3. Round | 23/11/2008 | Canterbury United | - | Waikato FC | 0:1 | ||||
4. Round | 29/11/2008 | Waitakere United | - | Canterbury United | 1:1 | ||||
5. Round | 07/12/2008 | Canterbury United | - | Team Wellington | 2:2 | ||||
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 | ||||
13. Round | 08/02/2009 | Canterbury United | - | Hawke’s Bay United FC | 0:4 |