| Saturday 8th August 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 2-3 | Colne | Att: 3 |
| Tuesday 11th August 2009 | Premier Division | ||
|---|---|---|---|
| Ashton Athletic | 2-3 | Winsford United | Att: 3 |
| Saturday 15th August 2009 | F.A. Challenge Cup Extra Preliminary Round | ||
|---|---|---|---|
| Flixton | 3-3 | Winsford United | Att: 3 |
| Tuesday 18th August 2009 | F.A. Challenge Cup Extra Preliminary Round Replay | ||
|---|---|---|---|
| Winsford United | 4-6 | Flixton | Att: 6 |
| Saturday 22nd August 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-3 | Formby | Att: 3 |
| Tuesday 25th August 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-4 | Glossop North End | Att: 4 |
| Saturday 29th August 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 3-0 | Squires Gate | Att: 0 |
| Tuesday 1st September 2009 | Premier Division | ||
|---|---|---|---|
| Bootle | 3-0 | Winsford United | Att: 0 |
| Saturday 5th September 2009 | Premier Division | ||
|---|---|---|---|
| Abbey Hey | 1-4 | Winsford United | Att: 4 |
| Tuesday 8th September 2009 | Premier Division | ||
|---|---|---|---|
| Alsager Town | 1-2 | Winsford United | Att: 2 |
| Saturday 12th September 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-3 | Silsden | Att: 3 |
| Saturday 19th September 2009 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Winsford United | 1-0 | Parkgate | Att: 0 |
| Saturday 26th September 2009 | Premier Division | ||
|---|---|---|---|
| Padiham | 1-3 | Winsford United | Att: 3 |
| Saturday 3rd October 2009 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Oldham Boro | 0-1 | Winsford United | Att: 1 |
| Tuesday 6th October 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-1 | Newcastle Town | Att: 1 |
| Saturday 10th October 2009 | Premier Division | ||
|---|---|---|---|
| Congleton Town | 3-0 | Winsford United | Att: 0 |
| Tuesday 13th October 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-3 | Bootle | Att: 3 |
| Saturday 17th October 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-3 | Atherton LR | Att: 3 |
| Saturday 24th October 2009 | Premier Division | ||
|---|---|---|---|
| New Mills | 4-1 | Winsford United | Att: 1 |
| Tuesday 27th October 2009 | Mid Cheshire Senior Cup Quarter Finals | ||
|---|---|---|---|
| Winsford United | 2-2 | Congleton Town | Att: 2 |
| (After Extra Time, Winsford United won 5-4 on penalties) | |||
| Saturday 31st October 2009 | League Challenge Cup 2nd Round | ||
|---|---|---|---|
| Winsford United | 3-2 | Maine Road | Att: 2 |
| Tuesday 10th November 2009 | Cheshire Senior Cup 1st Round | ||
|---|---|---|---|
| Winsford United | 2-3 | Cammell Laird | Att: 3 |
| Saturday 14th November 2009 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Winsford United | 1-2 | Pickering Town | Att: 2 |
| Saturday 21st November 2009 | Premier Division | ||
|---|---|---|---|
| Maine Road | 2-1 | Winsford United | Att: 1 |
| Saturday 28th November 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 3-2 | Ashton Athletic | Att: 2 |
| Tuesday 8th December 2009 | Premier Division | ||
|---|---|---|---|
| Newcastle Town | 3-2 | Winsford United | Att: 2 |
| Saturday 12th December 2009 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-2 | Nelson | Att: 2 |
| Wednesday 16th December 2009 | Premier Division | ||
|---|---|---|---|
| Glossop North End | 2-2 | Winsford United | Att: 2 |
| Saturday 23rd January 2010 | League Challenge Cup 3rd Round | ||
|---|---|---|---|
| Winsford United | 2-0 | Bacup Borough | Att: 0 |
| Saturday 30th January 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-2 | Maine Road | Att: 2 |
| Saturday 6th February 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-1 | Flixton | Att: 1 |
| Tuesday 9th February 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-1 | Alsager Town | Att: 1 |
| Saturday 13th February 2010 | Premier Division | ||
|---|---|---|---|
| Flixton | 2-2 | Winsford United | Att: 2 |
| Saturday 20th February 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-5 | Abbey Hey | Att: 5 |
| Tuesday 2nd March 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-3 | Congleton Town | Att: 3 |
| Saturday 6th March 2010 | Premier Division | ||
|---|---|---|---|
| Nelson | 2-1 | Winsford United | Att: 1 |
| Tuesday 9th March 2010 | Premier Division | ||
|---|---|---|---|
| Formby | 5-1 | Winsford United | Att: 1 |
| Saturday 13th March 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 1-0 | Runcorn Linnets | Att: 0 |
| Tuesday 16th March 2010 | League Challenge Cup Quarter Finals | ||
|---|---|---|---|
| Winsford United | 5-2 | Glossop North End | Att: 2 |
| Tuesday 23rd March 2010 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 0-0 | Winsford United | Att: 0 |
| Saturday 27th March 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 3-0 | Padiham | Att: 0 |
| Tuesday 30th March 2010 | Mid Cheshire Senior Cup Semi Finals | ||
|---|---|---|---|
| Winsford United | 1-0 | Barnton | Att: 0 |
| Saturday 3rd April 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-0 | Bacup Borough | Att: 0 |
| Monday 5th April 2010 | Premier Division | ||
|---|---|---|---|
| Runcorn Linnets | 0-3 | Winsford United | Att: 3 |
| Saturday 10th April 2010 | League Challenge Cup Semi Finals | ||
|---|---|---|---|
| Winsford United | 1-0 | St Helens Town | Att: 0 |
| Tuesday 13th April 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-1 | New Mills | Att: 1 |
| Saturday 17th April 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 0-2 | Ramsbottom United | Att: 2 |
| Tuesday 20th April 2010 | Premier Division | ||
|---|---|---|---|
| Ramsbottom United | 1-0 | Winsford United | Att: 0 |
| Thursday 22nd April 2010 | Mid Cheshire Senior Cup Final | ||
|---|---|---|---|
| Northwich Victoria | 4-0 | Winsford United | Att: 0 |
| Saturday 24th April 2010 | Premier Division | ||
|---|---|---|---|
| Silsden | 2-1 | Winsford United | Att: 1 |
| Tuesday 27th April 2010 | Premier Division | ||
|---|---|---|---|
| Squires Gate | 1-0 | Winsford United | Att: 0 |
| Thursday 29th April 2010 | Premier Division | ||
|---|---|---|---|
| Colne | 3-1 | Winsford United | Att: 1 |
| Saturday 1st May 2010 | Premier Division | ||
|---|---|---|---|
| Winsford United | 2-0 | St Helens Town | Att: 0 |
| Monday 3rd May 2010 | Premier Division | ||
|---|---|---|---|
| Atherton LR | 0-2 | Winsford United | Att: 2 |
| Thursday 6th May 2010 | League Challenge Cup Final | ||
|---|---|---|---|
| Abbey Hey | 3-0 | Winsford United | Att: 0 |
| Saturday 8th May 2010 | Premier Division | ||
|---|---|---|---|
| Bacup Borough | 2-2 | Winsford United | Att: 2 |
