5. Round | 07/12/2008 | Canterbury United | - | Team Wellington | 2:2 | ||||
7. Round | 21/12/2008 | Canterbury United | - | Auckland City FC | 2:1 | ||||
8. Round | 10/01/2009 | YoungHeart Manawatu | - | Canterbury United | 4:0 | ||||
9. Round | 18/01/2009 | Canterbury United | - | Otago United | 1:2 | ||||
10. Round | 23/01/2009 | Waikato FC | - | Canterbury United | 3:1 |