| 1. Round | 09/11/2008 | Auckland City FC | - | Otago United | 2:0 |  |
|||
| 2. Round | 15/11/2008 | Waikato FC | - | Auckland City FC | 1:3 | ||||
| 3. Round | 26/11/2008 | Auckland City FC | - | Waitakere United | 1:2 | ||||
| 4. Round | 29/11/2008 | Team Wellington | - | Auckland City FC | 2:1 | ||||
| 5. Round | 07/12/2008 | Auckland City FC | - | Hawke’s Bay United FC | 3:1 | ||||
| 7. Round | 21/12/2008 | Canterbury United | - | Auckland City FC | 2:1 | ||||
| 8. Round | 11/01/2009 | Otago United | - | Auckland City FC | 0:1 | ||||
| 9. Round | 17/01/2009 | Auckland City FC | - | Waikato FC | 3:0 | |
 |
||
| 10. Round | 24/01/2009 | Waitakere United | - | Auckland City FC | 4:2 | |
|||
| 11. Round | 31/01/2009 | Auckland City FC | - | Team Wellington | 1:3 | |
|||
| 12. Round | 06/02/2009 | Hawke’s Bay United FC | - | Auckland City FC | 0:1 | ||||
| 13. Round | 08/02/2009 | Auckland City FC | - | YoungHeart Manawatu | 3:0 | |
USA