| PRELIMINARY ROUND - 19/10/08 | ||||
| GAME | HOME | AWAY | ||
| 1 | Droylsden Juniors B | 5 | 1 | Marple Athletic |
| 2 | Inter Cheadle | 0 | 4 | Torpedo Grove |
| 3 | Stockport Vikings A | 10 | 1 | FC Didsbury Villa |
| 4 | Richmond Rovers A | 5 | 0 | Richmond Rovers B |
| 5 | FC Blue Star B | 2 | 10 | Apollo Juniors |
| 6 | Norbury Athletic | 2 | 9 | Hillgate Boys A |
| 7 | Chinley Juniors | 3 | 9 | Stockport Dynamoes |
| 8 | Stockport Junior Blues A | 7 | 1 | Reddish Vulcan Comets |
| 9 | Lisbon St Anthonys | 4 | 3 | Henbury & Broken Cross |
| 10 | Lostock Rangers | 2 | 6 | Mountfield Rovers |
| 11 | Signol Athletic | 2 | 0 | High Lane Juniors |
| 12 | Great Moor County | 1 | 3 | Cheadle & Gatley A |
| 13 | Cheadle & Gatley B | 7 | 3 | Reddish Athletic |
| 14 | Hollingworth Juniors | W | L | Hillgate Boys B |
| 15 | Reddish Vulcan Bombers | 10 | 1 | Queensgate Juniors |
| ROUND ONE - 23/11/08 | ||||
| GAME | HOME | AWAY | ||
| 1 | Rose Hill Rovers | 1 | 3 | Whaley Bridge Juniors |
| 2 | Hale United | Bramhall North 75 | ||
| 3 | Bollington United | 3 | 5 | Bramhall Lions |
| 4 | Stockport Vikings A | 13 | 0 | Cheadle & Gatley B |
| 5 | Reddish Vulcan Bombers | 26 | 0 | FC Blue Star A |
| 6 | New Mills Juniors | Hillgate Boys A | ||
| 7 | West End Boys | 8 | 6 | Torpedo Grove |
| 8 | Mountfield Rovers | Bye | ||
| 9 | Stockport Junior Blues B | Stockport Junior Blues A | ||
| 10 | Lisbon St Anthonys | 10 | 1 | Apollo Juniors |
| 11 | Hollingworth Juniors | Poynton Juniors | ||
| 12 | Cheadle & Gatley A | Woodley Albion | ||
| 13 | Hazel Grove United | 6 | 1 | Stockport Dynamoes |
| 14 | Hyde Athletic | 3 | 1 | Droylsden Juniors A |
| 15 | Stockport Vikings B | 0 | 5 | Richmond Rovers A |
| 16 | Signol Athletic | 7 | 1 | Chapel Town |
| ROUND TWO - 11/01/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Signol Athletic | 4 | 3 | New Mills Juniors |
| 2 | Cheadle & Gatley A | 4 | 0 | Bramhall North 75 |
| 3 | Stockport Vikings A | Reddish Vulcan Bombers | ||
| 4 | West End Boys | 6 | 1 | Whaley Bridge |
| 5 | Bramhall Lions | 0 | 5 | Richmond Rovers A |
| 6 | Hyde Athletic | 6 | 1 | Lisbon St Anthonys |
| 7 | Mountfield Rovers | 2 | 7 | Hazel Grove United |
| 8 | Hollingworth Juniors | Stockport Junior Blues A | ||
| ROUND THREE - 08/02/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Hyde Athletic | Signol Athletic | ||
| 2 | West End Boys | Stockport Junior Blues A | ||
| 3 | Cheadle & Gatley A | Richmond Rovers A | ||
| 4 | Reddish Vulcans Bombers | Hazel Grove United | ||
| SEMI FINALS - 15/03/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | Reddish Vulcans Bombers or Hazel Grove | Hyde Athletic or Signol Athletic | ||
| 2 | Stockport Junior Blues A | Richmond Rovers A | ||
| FINAL - 19/04/09 | ||||
| GAME | HOME | AWAY | ||
| 1 | ||||