| 2. Jornada | 16.11.2008 | Otago United | - | Canterbury United | 2:1 | ||||
| 3. Jornada | 23.11.2008 | Canterbury United | - | Waikato FC | 0:1 | ||||
| 4. Jornada | 29.11.2008 | Waitakere United | - | Canterbury United | 1:1 | ||||
| 5. Jornada | 07.12.2008 | Canterbury United | - | Team Wellington | 2:2 | ||||
| 9. Jornada | 18.01.2009 | Canterbury United | - | Otago United | 1:2 | ||||
| 10. Jornada | 24.01.2009 | Waikato FC | - | Canterbury United | 3:1 | ||||
| 11. Jornada | 01.02.2009 | Canterbury United | - | Waitakere United | 0:2 | ||||
| 13. Jornada | 08.02.2009 | Canterbury United | - | Hawke’s Bay United FC | 0:4 | ||||
| 12. Jornada | 22.02.2009 | Team Wellington | - | Canterbury United | 3:1 | ||||
| 14. Jornada | 01.03.2009 | Auckland City FC | - | Canterbury United | 5:0 |  |
Inglaterra