| 1. Jornada | 09.11.2008 | Team Wellington | - | Waitakere United | 2:4 |  |
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| 2. Jornada | 15.11.2008 | YoungHeart Manawatu | - | Team Wellington | 3:0 | ||||
| 3. Jornada | 23.11.2008 | Hawke’s Bay United FC | - | Team Wellington | 1:2 |  |
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| 4. Jornada | 29.11.2008 | Team Wellington | - | Auckland City FC | 2:1 | |
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| 5. Jornada | 07.12.2008 | Canterbury United | - | Team Wellington | 2:2 | |
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| 6. Jornada | 14.12.2008 | Team Wellington | - | Otago United | 1:1 | |
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| 7. Jornada | 21.12.2008 | Waikato FC | - | Team Wellington | 2:0 | ||||
| 8. Jornada | 11.01.2009 | Waitakere United | - | Team Wellington | 2:0 | ||||
| 9. Jornada | 18.01.2009 | Team Wellington | - | YoungHeart Manawatu | 3:2 | |
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| 10. Jornada | 25.01.2009 | Team Wellington | - | Hawke’s Bay United FC | 2:5 | ||||
| 11. Jornada | 31.01.2009 | Auckland City FC | - | Team Wellington | 1:3 | |
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| 13. Jornada | 08.02.2009 | Otago United | - | Team Wellington | 2:4 | |
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| 12. Jornada | 22.02.2009 | Team Wellington | - | Canterbury United | 3:1 | |
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| 14. Jornada | 01.03.2009 | Team Wellington | - | Waikato FC | 4:1 | |
Costa Rica