| 6. Jornada | 14.12.2008 | Team Wellington | - | Otago United | 1:1 |  |
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| 7. Jornada | 21.12.2008 | Otago United | - | Hawke’s Bay United FC | 1:3 | |
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| 8. Jornada | 11.01.2009 | Otago United | - | Auckland City FC | 0:1 | ||||
| 9. Jornada | 18.01.2009 | Canterbury United | - | Otago United | 1:2 | ||||
| 10. Jornada | 24.01.2009 | YoungHeart Manawatu | - | Otago United | 2:0 | |
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| 11. Jornada | 01.02.2009 | Otago United | - | Waikato FC | 3:3 | ||||
| 12. Jornada | 06.02.2009 | Waitakere United | - | Otago United | 3:0 | ||||
| 13. Jornada | 08.02.2009 | Otago United | - | Team Wellington | 2:4 | |
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| 5. Jornada | 22.02.2009 | Otago United | - | Waitakere United | 2:3 | |
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| 14. Jornada | 01.03.2009 | Hawke’s Bay United FC | - | Otago United | 2:0 |
Escocia