| Saturday 9th August 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Norton United | Att: 0 |
| Wednesday 13th August 2008 | First Division | ||
|---|---|---|---|
| Stone Dominoes | 0-2 | Cheadle Town | Att: 2 |
| Saturday 16th August 2008 | F.A. Challenge Cup Extra Preliminary Round | ||
|---|---|---|---|
| Cheadle Town | 1-4 | Newcastle Town | Att: 72 |
| Saturday 23rd August 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 5-0 | Holker Old Boys | Att: 0 |
| Saturday 6th September 2008 | F.A. Carlsberg Vase 1st Qualifying Round | ||
|---|---|---|---|
| Worsbrough Bridge Athletic | 5-2 | Cheadle Town | Att: 40 |
| Wednesday 10th September 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 1-0 | Leek CSOB | Att: 0 |
| Saturday 13th September 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | AFC Blackpool | Att: 0 |
| Saturday 27th September 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 1-2 | Ashton Town | Att: 2 |
| Saturday 4th October 2008 | First Division | ||
|---|---|---|---|
| Darwen | 0-4 | Cheadle Town | Att: 4 |
| Saturday 18th October 2008 | First Division | ||
|---|---|---|---|
| Wigan Robin Park | 1-1 | Cheadle Town | Att: 1 |
| Saturday 25th October 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 1-2 | Padiham | Att: 2 |
| Tuesday 28th October 2008 | First Division | ||
|---|---|---|---|
| Oldham Town | 3-1 | Cheadle Town | Att: 1 |
| Saturday 1st November 2008 | First Division | ||
|---|---|---|---|
| Chadderton | 4-1 | Cheadle Town | Att: 1 |
| Saturday 15th November 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 5-2 | Daisy Hill | Att: 2 |
| Saturday 22nd November 2008 | First Division | ||
|---|---|---|---|
| Cheadle Town | 0-4 | Bootle | Att: 4 |
| Saturday 20th December 2008 | First Division | ||
|---|---|---|---|
| AFC Liverpool | 2-1 | Cheadle Town | Att: 1 |
| Friday 26th December 2008 | First Division | ||
|---|---|---|---|
| Irlam | 1-0 | Cheadle Town | Att: 0 |
| Saturday 3rd January 2009 | First Division | ||
|---|---|---|---|
| Norton United | 1-2 | Cheadle Town | Att: 2 |
| Saturday 17th January 2009 | First Division | ||
|---|---|---|---|
| Holker Old Boys | 2-2 | Cheadle Town | Att: 2 |
| Saturday 24th January 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Rochdale Town | Att: 0 |
| Saturday 31st January 2009 | First Division | ||
|---|---|---|---|
| Leek CSOB | 0-2 | Cheadle Town | Att: 2 |
| Saturday 7th February 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 0-1 | AFC Liverpool | Att: 1 |
| Saturday 14th February 2009 | First Division | ||
|---|---|---|---|
| Ashton Town | 2-3 | Cheadle Town | Att: 3 |
| Saturday 28th February 2009 | First Division | ||
|---|---|---|---|
| AFC Blackpool | 0-2 | Cheadle Town | Att: 2 |
| Saturday 7th March 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 1-1 | Chadderton | Att: 1 |
| Wednesday 18th March 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 0-2 | Stone Dominoes | Att: 2 |
| Saturday 21st March 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Wigan Robin Park | Att: 0 |
| Saturday 28th March 2009 | First Division | ||
|---|---|---|---|
| Eccleshall | 4-2 | Cheadle Town | Att: 2 |
| Tuesday 31st March 2009 | First Division | ||
|---|---|---|---|
| Rochdale Town | 0-2 | Cheadle Town | Att: 2 |
| Saturday 4th April 2009 | First Division | ||
|---|---|---|---|
| Bootle | 1-0 | Cheadle Town | Att: 0 |
| Wednesday 8th April 2009 | First Division | ||
|---|---|---|---|
| Padiham | 4-2 | Cheadle Town | Att: 2 |
| Saturday 11th April 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 1-2 | Irlam | Att: 2 |
| Wednesday 22nd April 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 0-0 | Eccleshall | Att: 0 |
| Saturday 25th April 2009 | First Division | ||
|---|---|---|---|
| Daisy Hill | 1-2 | Cheadle Town | Att: 2 |
| Wednesday 29th April 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 2-1 | Oldham Town | Att: 1 |
| Saturday 2nd May 2009 | First Division | ||
|---|---|---|---|
| Cheadle Town | 0-1 | Darwen | Att: 1 |
