1. Round | 09/11/2008 | Auckland City FC | - | Otago United | 2:0 | ||||
2. Round | 16/11/2008 | Otago United | - | Canterbury United | 2:1 | ||||
3. Round | 23/11/2008 | Otago United | - | YoungHeart Manawatu | 2:3 | ![]() |
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4. Round | 30/11/2008 | Waikato FC | - | Otago United | 3:1 | ![]() |
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11. Round | 01/02/2009 | Otago United | - | Waikato FC | 3:3 | ![]() |
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12. Round | 06/02/2009 | Waitakere United | - | Otago United | 3:0 | ||||
13. Round | 08/02/2009 | Otago United | - | Team Wellington | 2:4 | ![]() |
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5. Round | 22/02/2009 | Otago United | - | Waitakere United | 2:3 | ![]() |
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14. Round | 01/03/2009 | Hawke’s Bay United FC | - | Otago United | 2:0 | ![]() |