| Saturday 14th August 1999 | Premier Division | ||
|---|---|---|---|
| Newcastle Town | 2-1 | Skelmersdale United | |
| Tuesday 17th August 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 2-0 | Atherton Collieries | |
| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Skelmersdale United | 5-2 | Whitley Bay | |
| Saturday 28th August 1999 | Premier Division | ||
|---|---|---|---|
| Maine Road | 2-6 | Skelmersdale United | |
| Tuesday 31st August 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 1-1 | Vauxhall Motors | |
| Saturday 4th September 1999 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Bradford Park Avenue | 2-0 | Skelmersdale United | |
| Tuesday 7th September 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 4-0 | Great Harwood Town | |
| Saturday 11th September 1999 | F.A. Carlsberg Vase 1st Qualifying Round | ||
|---|---|---|---|
| Nelson | 0-6 | Skelmersdale United | |
| Tuesday 14th September 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 4-4 | Skelmersdale United | |
| Saturday 18th September 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 0-0 | Abbey Hey | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Shotton Comrades | 0-2 | Skelmersdale United | |
| Tuesday 5th October 1999 | Premier Division | ||
|---|---|---|---|
| Mossley | 1-1 | Skelmersdale United | |
| Saturday 9th October 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 1-0 | Ramsbottom United | |
| Tuesday 12th October 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 0-0 | Newcastle Town | |
| Saturday 16th October 1999 | Premier Division | ||
|---|---|---|---|
| Glossop North End | 0-2 | Skelmersdale United | |
| Tuesday 19th October 1999 | Premier Division | ||
|---|---|---|---|
| Bootle | 0-3 | Skelmersdale United | |
| Saturday 23rd October 1999 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Skelmersdale United | 2-0 | Glasshoughton Welfare | |
| Saturday 30th October 1999 | Premier Division | ||
|---|---|---|---|
| Atherton Collieries | 0-2 | Skelmersdale United | |
| Saturday 6th November 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 5-2 | Kidsgrove Athletic | |
| Tuesday 9th November 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 0-2 | Clitheroe | |
| Saturday 13th November 1999 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Abbey Hey | 1-2 | Skelmersdale United | |
| Saturday 20th November 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 6-0 | Leek CSOB | |
| Tuesday 23rd November 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 3-0 | Bootle | |
| Saturday 4th December 1999 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| Skelmersdale United | 3-2 | Hall Road Rangers | |
| Saturday 18th December 1999 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 0-3 | Rossendale United | |
| Monday 3rd January 2000 | Premier Division | ||
|---|---|---|---|
| Prescot Cables | 3-1 | Skelmersdale United | |
| Saturday 8th January 2000 | Premier Division | ||
|---|---|---|---|
| Great Harwood Town | 1-4 | Skelmersdale United | |
| Tuesday 11th January 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 1-1 | St Helens Town | |
| Tuesday 18th January 2000 | Premier Division | ||
|---|---|---|---|
| Atherton LR | 2-4 | Skelmersdale United | |
| Saturday 22nd January 2000 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Skelmersdale United | 2-3 | Taunton Town | |
| (After Extra Time, 2-2 after 90 mins) | |||
| Thursday 27th January 2000 | Premier Division | ||
|---|---|---|---|
| Nantwich Town | 1-1 | Skelmersdale United | |
| Saturday 29th January 2000 | Premier Division | ||
|---|---|---|---|
| Kidsgrove Athletic | 2-1 | Skelmersdale United | |
| Saturday 5th February 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 5-1 | Prescot Cables | |
| Tuesday 22nd February 2000 | Premier Division | ||
|---|---|---|---|
| Vauxhall Motors | 3-0 | Skelmersdale United | |
| Saturday 26th February 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 1-0 | Salford City | |
| Tuesday 29th February 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 3-1 | Atherton LR | |
| Saturday 4th March 2000 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 1-5 | Skelmersdale United | |
| Saturday 11th March 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 3-0 | Glossop North End | |
| Tuesday 14th March 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 0-1 | Fleetwood Freeport | |
| Saturday 18th March 2000 | Premier Division | ||
|---|---|---|---|
| Abbey Hey | 1-3 | Skelmersdale United | |
| Tuesday 21st March 2000 | Premier Division | ||
|---|---|---|---|
| Ramsbottom United | 3-1 | Skelmersdale United | |
| Saturday 25th March 2000 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-2 | Skelmersdale United | |
| Tuesday 4th April 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 3-0 | Cheadle Town | |
| Tuesday 11th April 2000 | Premier Division | ||
|---|---|---|---|
| Fleetwood Freeport | 2-0 | Skelmersdale United | |
| Thursday 13th April 2000 | Premier Division | ||
|---|---|---|---|
| Salford City | 2-2 | Skelmersdale United | |
| Saturday 15th April 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 1-4 | Mossley | |
| Tuesday 18th April 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 2-0 | Nantwich Town | |
| Monday 24th April 2000 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 3-1 | Maine Road | |
| Saturday 29th April 2000 | Premier Division | ||
|---|---|---|---|
| Rossendale United | 2-1 | Skelmersdale United | |
| Wednesday 3rd May 2000 | Premier Division | ||
|---|---|---|---|
| Leek CSOB | 3-3 | Skelmersdale United | |
