| PRELIMINARY ROUND - 19/10/08 | ||||
| GAME | HOME | AWAY | ||
| 1 | Great Moor County | 0 | 3 | Norbury Athletic |
| 2 | Hollingworth Juniors (won on penalties) | 4 | 3 | Cheadle & Gatley A |
| 3 | Stockport Junior Blues | 10 | 0 | Marple Athletic |
| 4 | Mountfield Rovers | 5 | 0 | Wilmslow Sports |
| ROUND ONE - 23/11/08 | ||||
| GAME | HOME | AWAY | ||
| 1 | Hazel Grove United A | New York Rovers | ||
| 2 | High Lane Juniors | New Mills Juniors | ||
| 3 | Alderly Edge Druids | Reddish North End | ||
| 4 | Norbury Athletic | Ryecroft Rangers | ||
| 5 | Reddish Vulcans B | Deltic FC | ||
| 6 | Hollingworth juniors | Woodley Albion | ||
| 7 | Droylsden Juniors | Poynton Juniors | ||
| 8 | Vale Rangers | Bollington United | ||
| 9 | Whaley Bridge Juniors | Hillgate Boys | ||
| 10 | FC Blue Star Rangers | Stockport Junior Blues | ||
| 11 | Sandringham Rovers | Hazel Grove United B | ||
| 12 | Lostock Rangers | Disley Juniors | ||
| 13 | A6 Juniors | Bramhall North 75 | ||
| 14 | Cheadle Heath Nomads | Signol Athletic | ||
| 15 | Cheadle & Gatley B | Reddish Vulcans A | ||
| 16 | Chinley Juniors | Mountfield Rovers | ||
| ROUND TWO - | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||
| 2 | ||||
| 3 | ||||
| 4 | ||||
| 5 | ||||
| 6 | ||||
| 7 | ||||
| 8 | ||||
| ROUND THREE | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||
| 2 | ||||
| 3 | ||||
| 4 | ||||
| SEMI FINALS | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||
| 2 | ||||
| FINAL | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||