2. Round | 16/11/2008 | Otago United | - | Canterbury United | 2:1 | ||||
3. Round | 23/11/2008 | Canterbury United | - | Waikato FC | 0:1 | ||||
11. Round | 01/02/2009 | Canterbury United | - | Waitakere United | 0:2 | ||||
13. Round | 08/02/2009 | Canterbury United | - | Hawke’s Bay United FC | 0:4 |