Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 11.01.2009 |  | Matchday 8 | Waitakere Utd. - Team Wellington | Wai - Tea | 2:0 | 523 |
| 18.01.2009 | | Matchday 9 | Waitakere Utd. - Hawke’s Bay Utd | Wai - Haw | 0:0 | 364 |
| 24.01.2009 | | Matchday 10 | Waitakere Utd. - Auckland City | Wai - AUC | 4:2 | 711 |
| 26.01.2009 | | Matchday 6 | Waitakere Utd. - WaiBOP United | Wai - Wai | 2:0 | 358 |
| 06.02.2009 | | Matchday 12 | Waitakere Utd. - Southern United | Wai - Ota | 3:0 | 223 |
| 21.03.2009 | | Semi-finals 2nd leg | Waitakere Utd. - Team Wellington | Wai - Tea | 5:0 | 403 |
| 29.03.2009 | | Final | Waitakere Utd. - Auckland City | Wai - AUC | 1:2 | 2.500 |