| 1. Round | 01/11/2014 | Canterbury United | - | WaiBOP United | 2:0 | ||||
| 3. Round | 16/11/2014 | Team Wellington | - | WaiBOP United | 3:2 | ||||
| 4. Round | 22/11/2014 | WaiBOP United | - | Wanderers SC | 0:3 dec. | ||||
| 6. Round | 06/12/2014 | WaiBOP United | - | Waitakere United | 1:1 |  |
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| 7. Round | 13/12/2014 | Wellington Phoenix (R) | - | WaiBOP United | 0:2 |  |
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| 8. Round | 20/12/2014 | WaiBOP United | - | Hawke’s Bay United FC | 2:4 | ||||
| 9. Round | 11/01/2015 | Southern United | - | WaiBOP United | 0:1 | ||||
| 10. Round | 17/01/2015 | WaiBOP United | - | Canterbury United | 4:3 | ||||
| 11. Round | 25/01/2015 | Auckland City FC | - | WaiBOP United | 3:2 | ||||
| 13. Round | 08/02/2015 | Wanderers SC | - | WaiBOP United | 1:2 | ||||
| 15. Round | 21/02/2015 | Waitakere United | - | WaiBOP United | 2:1 | |
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| 16. Round | 28/02/2015 | WaiBOP United | - | Wellington Phoenix (R) | 2:3 | |
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| 17. Round | 08/03/2015 | Hawke’s Bay United FC | - | WaiBOP United | 0:1 | ||||
| 18. Round | 14/03/2015 | WaiBOP United | - | Southern United | 2:1 |
Chile