3. Round | 23/11/2008 | Hawke’s Bay United FC | - | Team Wellington | 1:2 | ||||
4. Round | 29/11/2008 | Team Wellington | - | Auckland City FC | 2:1 | ||||
5. Round | 07/12/2008 | Canterbury United | - | Team Wellington | 2:2 | ||||
7. Round | 21/12/2008 | Waikato FC | - | Team Wellington | 2:0 | ||||
8. Round | 11/01/2009 | Waitakere United | - | Team Wellington | 2:0 | ||||
9. Round | 18/01/2009 | Team Wellington | - | YoungHeart Manawatu | 3:2 | ||||
10. Round | 25/01/2009 | Team Wellington | - | Hawke’s Bay United FC | 2:5 |