| PRELIMINARY ROUND - 19/10/08 | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||
| 2 | ||||
| 3 | ||||
| 4 | ||||
| ROUND ONE - 23/11/08 | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||
| 2 | ||||
| 3 | ||||
| 4 | ||||
| 5 | ||||
| 6 | ||||
| 7 | ||||
| 8 | ||||
| 9 | ||||
| 10 | ||||
| 11 | ||||
| 12 | ||||
| 13 | ||||
| 14 | ||||
| 15 | ||||
| 16 | ||||
| ROUND TWO - 11/01/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Juno United | 4 | 5 | Hale United A - AET Penalties |
| 2 | Hale United B | 7 | 2 | Inter Cheadle |
| 3 | Richmond Rovers | 5 | 6 | Signol Athletic |
| 4 | Brendon Bees | 3 | 1 | Bollington United |
| 5 | Cheadle Heath Nomads | 5 | 2 | Spurley Hey |
| 6 | Lostock Rangers A | Bye | ||
| 7 | Marple Athletic | Bye | ||
| 8 | Stockport Junior Blues | Bye | ||
| ROUND THREE - 08/02/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Brendon Bees | 2 | 0 | Lostock A |
| 2 | Hale United B | 1 | 0 | Cheadle Heath Nomads |
| 3 | Stockport Junior Blues | 1 | 2 | Hale United A |
| 4 | Signol Athletic | 4 | 2 | Marple Athletic |
| SEMI FINALS - 15/03/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Signol Athletic | Hale United A | ||
| 2 | Hale United B | Brendon Bees | ||
| FINAL - 19/04/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||