| 1. Jornada | 09.11.2008 | Auckland City FC | - | Otago United | 2:0 | ||||
| 2. Jornada | 16.11.2008 | Otago United | - | Canterbury United | 2:1 | ||||
| 3. Jornada | 23.11.2008 | Otago United | - | YoungHeart Manawatu | 2:3 | ||||
| 4. Jornada | 30.11.2008 | Waikato FC | - | Otago United | 3:1 |  |
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| 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 | ||||
| 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 | ||||
| 11. Jornada | 01.02.2009 | Otago United | - | Waikato FC | 3:3 | |
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| 12. Jornada | 06.02.2009 | Waitakere United | - | Otago United | 3:0 | ||||
| 5. Jornada | 22.02.2009 | Otago United | - | Waitakere United | 2:3 | |
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Inglaterra