| Saturday 15th August 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 0-1 | Leek CSOB | |
| Monday 17th August 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 5-0 | Cheadle Town | |
| Saturday 22nd August 1998 | Premier Division | ||
|---|---|---|---|
| Newcastle Town | 3-1 | Clitheroe | |
| Tuesday 25th August 1998 | Premier Division | ||
|---|---|---|---|
| Workington | 2-2 | Clitheroe | |
| Saturday 29th August 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 3-1 | Salford City | |
| Tuesday 1st September 1998 | Premier Division | ||
|---|---|---|---|
| Holker Old Boys | 2-5 | Clitheroe | |
| Saturday 5th September 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 0-0 | Newcastle Town | |
| Monday 7th September 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 3-1 | Atherton Collieries | |
| Saturday 12th September 1998 | Premier Division | ||
|---|---|---|---|
| Glossop North End | 1-0 | Clitheroe | |
| Tuesday 15th September 1998 | Premier Division | ||
|---|---|---|---|
| Salford City | 2-0 | Clitheroe | |
| Saturday 19th September 1998 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Radcliffe | 2-1 | Clitheroe | |
| Wednesday 23rd September 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 0-1 | Ramsbottom United | |
| Saturday 26th September 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 1-2 | Clitheroe | |
| Tuesday 29th September 1998 | Premier Division | ||
|---|---|---|---|
| Maine Road | 4-1 | Clitheroe | |
| Saturday 3rd October 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 0-0 | Vauxhall GM | |
| Saturday 10th October 1998 | Premier Division | ||
|---|---|---|---|
| Kidsgrove Athletic | 2-1 | Clitheroe | |
| Monday 12th October 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 3-1 | Rossendale United | |
| Saturday 17th October 1998 | Premier Division | ||
|---|---|---|---|
| Bootle | 1-2 | Clitheroe | |
| Saturday 31st October 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 3-1 | Kidsgrove Athletic | |
| Wednesday 11th November 1998 | Premier Division | ||
|---|---|---|---|
| Atherton Collieries | 1-1 | Clitheroe | |
| Saturday 14th November 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 2-3 | Prescot Cables | |
| Saturday 21st November 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 1-2 | St Helens Town | |
| Saturday 28th November 1998 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Clitheroe | 1-0 | West Auckland Town | |
| (After Extra Time, 0-0 after 90 mins) | |||
| Saturday 12th December 1998 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| Billingham Town | 0-2 | Clitheroe | |
| Saturday 19th December 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 6-0 | Bootle | |
| Saturday 2nd January 1999 | Premier Division | ||
|---|---|---|---|
| Atherton LR | 1-0 | Clitheroe | |
| Saturday 23rd January 1999 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Clitheroe | 1-0 | St Helens Town | |
| Premier Division | |||
|---|---|---|---|
| Skelmersdale United | 1-1 | Clitheroe |
| Saturday 6th February 1999 | F.A. Carlsberg Vase 5th Round | ||
|---|---|---|---|
| Clitheroe | 1-0 | Bemerton Heath Harlequins | |
| Premier Division | |||
|---|---|---|---|
| Mossley | 1-0 | Clitheroe |
| Saturday 20th February 1999 | F.A. Carlsberg Vase Quarter Finals | ||
|---|---|---|---|
| Tiverton Town | 4-0 | Clitheroe | |
| Saturday 27th February 1999 | Premier Division | ||
|---|---|---|---|
| Nantwich Town | 1-2 | Clitheroe | |
| Saturday 13th March 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 5-1 | Glossop North End | |
| Monday 15th March 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 5-1 | Holker Old Boys | |
| Saturday 20th March 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 0-2 | Skelmersdale United | |
| Saturday 27th March 1999 | Premier Division | ||
|---|---|---|---|
| Leek CSOB | 3-1 | Clitheroe | |
| Saturday 3rd April 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 1-3 | Mossley | |
| Saturday 10th April 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 4-0 | Atherton LR | |
| Monday 12th April 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 0-1 | Workington | |
| Saturday 17th April 1999 | Premier Division | ||
|---|---|---|---|
| Prescot Cables | 1-0 | Clitheroe | |
| Monday 26th April 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 1-3 | Nantwich Town | |
| Thursday 29th April 1999 | Premier Division | ||
|---|---|---|---|
| Rossendale United | 2-1 | Clitheroe | |
| Saturday 1st May 1999 | Premier Division | ||
|---|---|---|---|
| Vauxhall GM | 2-0 | Clitheroe | |
| Monday 3rd May 1999 | Premier Division | ||
|---|---|---|---|
| Ramsbottom United | 0-1 | Clitheroe | |
| Wednesday 5th May 1999 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 2-0 | Clitheroe | |
| Saturday 8th May 1999 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 4-1 | Maine Road | |
