1. Round | 09/11/2008 | Team Wellington | - | Waitakere United | 2:4 | ||||
3. Round | 26/11/2008 | Auckland City FC | - | Waitakere United | 1:2 | ||||
4. Round | 29/11/2008 | Waitakere United | - | Canterbury United | 1:1 | ||||
7. Round | 21/12/2008 | Waitakere United | - | YoungHeart Manawatu | 3:0 | ||||
8. Round | 11/01/2009 | Waitakere United | - | Team Wellington | 2:0 | ||||
9. Round | 18/01/2009 | Waitakere United | - | Hawke’s Bay United FC | 0:0 | ||||
2. Round | 15/02/2009 | Hawke’s Bay United FC | - | Waitakere United | 0:1 | ||||
5. Round | 22/02/2009 | Otago United | - | Waitakere United | 2:3 |