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