1. Round | 09/11/2008 | Auckland City FC | - | Otago United | 2:0 | ||||
2. Round | 16/11/2008 | Otago United | - | Canterbury United | 2:1 | ||||
3. Round | 23/11/2008 | Otago United | - | YoungHeart Manawatu | 2:3 | ||||
4. Round | 30/11/2008 | Waikato FC | - | Otago United | 3:1 | ||||
6. Round | 14/12/2008 | Team Wellington | - | Otago United | 1:1 | ||||
7. Round | 21/12/2008 | Otago United | - | Hawke’s Bay United FC | 1:3 | ||||
8. Round | 11/01/2009 | Otago United | - | Auckland City FC | 0:1 | ||||
9. Round | 18/01/2009 | Canterbury United | - | Otago United | 1:2 | ||||
11. Round | 01/02/2009 | Otago United | - | Waikato FC | 3:3 | ||||
12. Round | 06/02/2009 | Waitakere United | - | Otago United | 3:0 | ||||
13. Round | 08/02/2009 | Otago United | - | Team Wellington | 2:4 | ||||
5. Round | 22/02/2009 | Otago United | - | Waitakere United | 2:3 |