| 1. Ronde | 08.11.2008 | Canterbury United | - | YoungHeart Manawatu | 0:1 | ||||
| 4. Ronde | 29.11.2008 | Waitakere United | - | Canterbury United | 1:1 | ||||
| 6. Ronde | 14.12.2008 | Hawke’s Bay United FC | - | Canterbury United | 1:2 | ||||
| 7. Ronde | 21.12.2008 | Canterbury United | - | Auckland City FC | 2:1 | ||||
| 9. Ronde | 18.01.2009 | Canterbury United | - | Otago United | 1:2 | ||||
| 11. Ronde | 01.02.2009 | Canterbury United | - | Waitakere United | 0:2 | ||||
| 12. Ronde | 22.02.2009 | Team Wellington | - | Canterbury United | 3:1 |
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