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