| Saturday 15th August 1998 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 4-1 | Cheadle Town | |
| Monday 17th August 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 5-0 | Cheadle Town | |
| Saturday 22nd August 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 5-1 | Atherton LR | |
| Tuesday 25th August 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-1 | Nantwich Town | |
| Saturday 29th August 1998 | Premier Division | ||
|---|---|---|---|
| Mossley | 3-1 | Cheadle Town | |
| Tuesday 1st September 1998 | Premier Division | ||
|---|---|---|---|
| Kidsgrove Athletic | 0-0 | Cheadle Town | |
| Saturday 5th September 1998 | Premier Division | ||
|---|---|---|---|
| Glossop North End | 1-3 | Cheadle Town | |
| Tuesday 8th September 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-1 | Leek CSOB | |
| Saturday 12th September 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 0-5 | St Helens Town | |
| Saturday 19th September 1998 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Parkgate | 4-2 | Cheadle Town | |
| Saturday 26th September 1998 | Premier Division | ||
|---|---|---|---|
| Nantwich Town | 2-1 | Cheadle Town | |
| Tuesday 29th September 1998 | Premier Division | ||
|---|---|---|---|
| Bootle | 1-2 | Cheadle Town | |
| Saturday 3rd October 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-1 | Workington | |
| Saturday 10th October 1998 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Cheadle Town | 2-3 | Ramsbottom United | |
| Saturday 17th October 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 3-3 | Rossendale United | |
| Saturday 31st October 1998 | Premier Division | ||
|---|---|---|---|
| Ramsbottom United | 4-2 | Cheadle Town | |
| Saturday 7th November 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-6 | Atherton Collieries | |
| Saturday 14th November 1998 | Premier Division | ||
|---|---|---|---|
| Newcastle Town | 2-0 | Cheadle Town | |
| Saturday 21st November 1998 | Premier Division | ||
|---|---|---|---|
| Prescot Cables | 3-1 | Cheadle Town | |
| Saturday 28th November 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-0 | Holker Old Boys | |
| Saturday 12th December 1998 | Premier Division | ||
|---|---|---|---|
| Atherton Collieries | 0-2 | Cheadle Town | |
| Saturday 19th December 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-6 | Prescot Cables | |
| Saturday 26th December 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-6 | Vauxhall GM | |
| Monday 28th December 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 0-4 | Maine Road | |
| Saturday 2nd January 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 0-4 | Salford City | |
| Tuesday 5th January 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 0-3 | Mossley | |
| Saturday 16th January 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Skelmersdale United | |
| Saturday 23rd January 1999 | Premier Division | ||
|---|---|---|---|
| Atherton LR | 1-1 | Cheadle Town | |
| Wednesday 27th January 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 4-1 | Cheadle Town | |
| Saturday 30th January 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Newcastle Town | |
| Saturday 6th February 1999 | Premier Division | ||
|---|---|---|---|
| Holker Old Boys | 2-4 | Cheadle Town | |
| Saturday 20th February 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 1-2 | Ramsbottom United | |
| Saturday 27th February 1999 | Premier Division | ||
|---|---|---|---|
| Rossendale United | 3-2 | Cheadle Town | |
| Tuesday 9th March 1999 | Premier Division | ||
|---|---|---|---|
| Leek CSOB | 2-0 | Cheadle Town | |
| Saturday 13th March 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-3 | Bootle | |
| Saturday 20th March 1999 | Premier Division | ||
|---|---|---|---|
| Salford City | 1-4 | Cheadle Town | |
| Tuesday 23rd March 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 0-2 | Kidsgrove Athletic | |
| Saturday 3rd April 1999 | Premier Division | ||
|---|---|---|---|
| Maine Road | 0-0 | Cheadle Town | |
| Monday 5th April 1999 | Premier Division | ||
|---|---|---|---|
| Vauxhall GM | 5-2 | Cheadle Town | |
| Saturday 17th April 1999 | Premier Division | ||
|---|---|---|---|
| Workington | 6-1 | Cheadle Town | |
| Tuesday 27th April 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Glossop North End | |
| Wednesday 5th May 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Clitheroe | |
