1. Round | 09/11/2008 | Team Wellington | - | Waitakere United | 2:4 | ||||
2. Round | 15/11/2008 | YoungHeart Manawatu | - | Team Wellington | 3:0 | ||||
3. Round | 23/11/2008 | Hawke’s Bay United FC | - | Team Wellington | 1:2 | ||||
5. Round | 07/12/2008 | Canterbury United | - | Team Wellington | 2:2 | ||||
6. Round | 14/12/2008 | Team Wellington | - | Otago United | 1:1 | ||||
7. Round | 21/12/2008 | Waikato FC | - | Team Wellington | 2:0 | ||||
11. Round | 31/01/2009 | Auckland City FC | - | Team Wellington | 1:3 | ||||
13. Round | 08/02/2009 | Otago United | - | Team Wellington | 2:4 | ||||
12. Round | 22/02/2009 | Team Wellington | - | Canterbury United | 3:1 |