| 1. Round | 09/11/2008 | Auckland City FC | - | Otago United | 2:0 |  |
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| 2. Round | 16/11/2008 | Otago United | - | Canterbury United | 2:1 | ||||
| 3. Round | 23/11/2008 | Otago United | - | YoungHeart Manawatu | 2:3 | ||||
| 4. Round | 30/11/2008 | Waikato FC | - | Otago United | 3:1 | ||||
| 6. Round | 14/12/2008 | Team Wellington | - | Otago United | 1:1 | ||||
| 7. Round | 21/12/2008 | Otago United | - | Hawke’s Bay United FC | 1:3 | ||||
| 8. Round | 11/01/2009 | Otago United | - | Auckland City FC | 0:1 | |
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| 9. Round | 18/01/2009 | Canterbury United | - | Otago United | 1:2 | ||||
| 11. Round | 01/02/2009 | Otago United | - | Waikato FC | 3:3 | ||||
| 12. Round | 06/02/2009 | Waitakere United | - | Otago United | 3:0 | ||||
| 13. Round | 08/02/2009 | Otago United | - | Team Wellington | 2:4 | ||||
| 5. Round | 22/02/2009 | Otago United | - | Waitakere United | 2:3 | ||||
| 14. Round | 01/03/2009 | Hawke’s Bay United FC | - | Otago United | 2:0 |
New Zealand