| 3. Jornada | 23.11.2008 | Canterbury United | - | Waikato FC | 0:1 | ||||
| 4. Jornada | 29.11.2008 | Waitakere United | - | Canterbury United | 1:1 |  |
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| 5. Jornada | 07.12.2008 | Canterbury United | - | Team Wellington | 2:2 |  |
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| 6. Jornada | 14.12.2008 | Hawke’s Bay United FC | - | Canterbury United | 1:2 | ||||
| 7. Jornada | 21.12.2008 | Canterbury United | - | Auckland City FC | 2:1 | ||||
| 8. Jornada | 10.01.2009 | YoungHeart Manawatu | - | Canterbury United | 4:0 | ||||
| 9. Jornada | 18.01.2009 | Canterbury United | - | Otago United | 1:2 | ||||
| 10. Jornada | 24.01.2009 | Waikato FC | - | Canterbury United | 3:1 | |
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| 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 | |
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| 14. Jornada | 01.03.2009 | Auckland City FC | - | Canterbury United | 5:0 |
Inglaterra