| Saturday 9th August 2008 | Premier Division | ||
|---|---|---|---|
| Bacup Borough | 0-2 | Winsford United | Att: 2 |
| Tuesday 12th August 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 5-2 | Flixton | Att: 2 |
| Saturday 16th August 2008 | F.A. Challenge Cup Extra Preliminary Round | ||
|---|---|---|---|
| Winsford United | 3-3 | Nostell Miners Welfare | Att: 130 |
| Tuesday 19th August 2008 | F.A. Challenge Cup Extra Preliminary Round Replay | ||
|---|---|---|---|
| Nostell Miners Welfare | 3-0 | Winsford United | Att: 135 |
| Saturday 23rd August 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-0 | Squires Gate | Att: 0 |
| Saturday 30th August 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-2 | Abbey Hey | Att: 2 |
| Saturday 13th September 2008 | Premier Division | ||
|---|---|---|---|
| Atherton Collieries | 0-4 | Winsford United | Att: 4 |
| Tuesday 16th September 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-2 | Formby | Att: 2 |
| Saturday 20th September 2008 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Hallam | 3-2 | Winsford United | Att: 58 |
| Saturday 27th September 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 2-0 | Maine Road | Att: 0 |
| Saturday 4th October 2008 | Premier Division | ||
|---|---|---|---|
| Silsden | 1-0 | Winsford United | Att: 0 |
| Tuesday 7th October 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-3 | Newcastle Town | Att: 3 |
| Saturday 11th October 2008 | Premier Division | ||
|---|---|---|---|
| AFC Fylde | 5-1 | Winsford United | Att: 1 |
| Tuesday 14th October 2008 | Premier Division | ||
|---|---|---|---|
| Maine Road | 2-2 | Winsford United | Att: 2 |
| Saturday 25th October 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 2-2 | Atherton LR | Att: 2 |
| Wednesday 29th October 2008 | Premier Division | ||
|---|---|---|---|
| Glossop North End | 4-0 | Winsford United | Att: 0 |
| Saturday 1st November 2008 | Premier Division | ||
|---|---|---|---|
| Formby | 0-1 | Winsford United | Att: 1 |
| Saturday 15th November 2008 | Premier Division | ||
|---|---|---|---|
| Ashton Athletic | 2-2 | Winsford United | Att: 2 |
| Tuesday 18th November 2008 | Premier Division | ||
|---|---|---|---|
| Newcastle Town | 2-0 | Winsford United | Att: 0 |
| Saturday 22nd November 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-1 | Colne | Att: 1 |
| Tuesday 25th November 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-4 | Congleton Town | Att: 4 |
| Saturday 29th November 2008 | Premier Division | ||
|---|---|---|---|
| Runcorn Linnets | 0-2 | Winsford United | Att: 2 |
| Saturday 6th December 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 3-2 | Atherton Collieries | Att: 2 |
| Saturday 13th December 2008 | Premier Division | ||
|---|---|---|---|
| Squires Gate | 1-0 | Winsford United | Att: 0 |
| Saturday 20th December 2008 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-5 | Nelson | Att: 5 |
| Friday 26th December 2008 | Premier Division | ||
|---|---|---|---|
| Alsager Town | 2-1 | Winsford United | Att: 1 |
| Saturday 3rd January 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-3 | Glossop North End | Att: 3 |
| Saturday 17th January 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-2 | New Mills | Att: 2 |
| Saturday 31st January 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-2 | Runcorn Linnets | Att: 2 |
| Saturday 14th February 2009 | Premier Division | ||
|---|---|---|---|
| Atherton LR | 2-2 | Winsford United | Att: 2 |
| Saturday 21st February 2009 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 2-1 | Winsford United | Att: 1 |
| Saturday 28th February 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-0 | Bacup Borough | Att: 0 |
| Tuesday 3rd March 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-2 | St Helens Town | Att: 2 |
| Saturday 7th March 2009 | Premier Division | ||
|---|---|---|---|
| New Mills | 3-0 | Winsford United | Att: 0 |
| Saturday 14th March 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-2 | Ashton Athletic | Att: 2 |
| Tuesday 17th March 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 2-2 | Ramsbottom United | Att: 2 |
| Saturday 21st March 2009 | Premier Division | ||
|---|---|---|---|
| Colne | 3-2 | Winsford United | Att: 2 |
| Saturday 28th March 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-5 | AFC Fylde | Att: 5 |
| Tuesday 31st March 2009 | Premier Division | ||
|---|---|---|---|
| Ramsbottom United | 1-2 | Winsford United | Att: 2 |
| Saturday 4th April 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-1 | Silsden | Att: 1 |
| Saturday 11th April 2009 | Premier Division | ||
|---|---|---|---|
| Congleton Town | 4-1 | Winsford United | Att: 1 |
| Monday 13th April 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-1 | Alsager Town | Att: 1 |
| Saturday 18th April 2009 | Premier Division | ||
|---|---|---|---|
| Nelson | 2-2 | Winsford United | Att: 2 |
| Tuesday 21st April 2009 | Premier Division | ||
|---|---|---|---|
| Abbey Hey | 1-4 | Winsford United | Att: 4 |
| Saturday 2nd May 2009 | Premier Division | ||
|---|---|---|---|
| Flixton | 2-1 | Winsford United | Att: 1 |
