| 1. Round | 02/11/2014 | Team Wellington | - | Wellington Phoenix (R) | 2:1 | ||||
| 2. Round | 09/11/2014 | Hawke’s Bay United FC | - | Team Wellington | 2:2 | ||||
| 3. Round | 16/11/2014 | Team Wellington | - | WaiBOP United | 3:2 | ||||
| 4. Round | 23/11/2014 | Canterbury United | - | Team Wellington | 2:2 | ||||
| 5. Round | 29/11/2014 | Team Wellington | - | Auckland City FC | 4:0 | ||||
| 6. Round | 07/12/2014 | Team Wellington | - | Southern United | 2:0 | ||||
| 7. Round | 14/12/2014 | Wanderers SC | - | Team Wellington | 1:4 | ||||
| 9. Round | 11/01/2015 | Team Wellington | - | Waitakere United | 1:2 | ||||
| 10. Round | 17/01/2015 | Wellington Phoenix (R) | - | Team Wellington | 3:4 | ||||
| 11. Round | 25/01/2015 | Team Wellington | - | Hawke’s Bay United FC | 1:0 | ||||
| 12. Round | 31/01/2015 | WaiBOP United | - | Team Wellington | 2:1 | ||||
| 13. Round | 08/02/2015 | Team Wellington | - | Canterbury United | 3:0 | ||||
| 14. Round | 15/02/2015 | Auckland City FC | - | Team Wellington | 3:0 |
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