| 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 | 10 | 0 | New York Rovers |
| 2 | High Lane Juniors | 0 | 2 | New Mills Juniors |
| 3 | Alderly Edge Druids | 5 | 1 | Reddish North End |
| 4 | Norbury Athletic | 8 | 9 | Ryecroft Rangers |
| 5 | Reddish Vulcans B | 0 | 2 | Deltic FC |
| 6 | Hollingworth juniors | 4 | 1 | Woodley Albion |
| 7 | Droylsden Juniors | 0 | 5 | Poynton Juniors |
| 8 | Vale Rangers | 6 | 2 | Bollington United |
| 9 | Whaley Bridge Juniors | 1 | 3 | Hillgate Boys |
| 10 | FC Blue Star Rangers | 0 | 7 | Stockport Junior Blues |
| 11 | Sandringham Rovers | 0 | 8 | Hazel Grove United B |
| 12 | Lostock Rangers | 4 | 1 | Disley Juniors |
| 13 | A6 Juniors | 2 | 1 | Bramhall North 75 |
| 14 | Cheadle Heath Nomads | 1 | 2 | Signol Athletic |
| 15 | Cheadle & Gatley B | 0 | 13 | Reddish Vulcans A |
| 16 | Chinley Juniors | 0 | 8 | Mountfield Rovers |
| ROUND TWO - 11/01/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Signol Athletic | 3 | 4 | Ryecroft Rangers |
| 2 | Vale Rangers | 2 | 5 | Hillgate Boys |
| 3 | Stockport Junior Blues | 3 | 8 | Hollingworth Juniors |
| 4 | Deltic FC | 0 | 1 | Alderley Edge Druids |
| 5 | Hazel Grove United B | 0 | 2 | New Mils Juniors |
| 6 | Lostock Rangers | 1 | 10 | Mountfield Rovers |
| 7 | A6 Juniors | 1 | 6 | Poynton Juniors |
| 8 | Hazel Grove United A | 6 | 4 | Reddish Vulcans A |
| ROUND THREE - 08/02/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Alderley Edge Druids | 5 | 1 | Hillgate Boys |
| 2 | Hazel Grove United A | 6 | 2 | New Mills Juniors |
| 3 | Mountfield Rovers | 2 | 0 | Hollingworth Juniors |
| 4 | Poynton Juniors | Ryecroft Rangers | ||
| SEMI FINALS - 15/03/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Poynton Juniors or Ryecroft Rangers | Alderley Edge Druids | ||
| 2 | Mountfield Rovers | Hazel Grove United A | ||
| FINAL - 19/04/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||