| Saturday 15th August 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 1-2 | Newcastle Town | |
| Saturday 22nd August 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Leek CSOB | 1-1 | Workington | |
| Tuesday 25th August 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 2-2 | Clitheroe | |
| Saturday 29th August 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 0-0 | Glossop North End | |
| Monday 31st August 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Nantwich Town | 0-2 | Workington | |
| Saturday 5th September 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Skelmersdale United | 1-0 | Workington | |
| Tuesday 8th September 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Rossendale United | 0-1 | Workington | |
| Saturday 12th September 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Prescot Cables | 0-0 | Workington | |
| Tuesday 15th September 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Maine Road | 0-1 | Workington | |
| Saturday 19th September 1998 | |||
|---|---|---|---|
| F.A. Challenge Cup 1st Qualifying Round | |||
| Ossett Albion | 4-2 | Workington | |
| Saturday 26th September 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 1-0 | Vauxhall GM | |
| Tuesday 29th September 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Salford City | 1-2 | Workington | |
| Saturday 3rd October 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Cheadle Town | 1-1 | Workington | |
| Saturday 10th October 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Mossley | 0-3 | Workington | |
| Wednesday 14th October 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Ramsbottom United | 0-0 | Workington | |
| Saturday 17th October 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 3-1 | Kidsgrove Athletic | |
| Saturday 31st October 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 2-2 | Leek CSOB | |
| Saturday 7th November 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 1-1 | Skelmersdale United | |
| Saturday 14th November 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 3-2 | Nantwich Town | |
| Saturday 21st November 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Bootle | 0-2 | Workington | |
| Saturday 28th November 1998 | |||
|---|---|---|---|
| F.A. Carlsberg Vase 2nd Round | |||
| North Ferriby United | 0-1 | Workington | |
| Saturday 12th December 1998 | |||
|---|---|---|---|
| F.A. Carlsberg Vase 3rd Round | |||
| Workington | 1-1 | Tow Law Town | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Tuesday 15th December 1998 | |||
|---|---|---|---|
| F.A. Carlsberg Vase | |||
| Tow Law Town | 3-4 | Workington | |
| Saturday 19th December 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 4-0 | Atherton Collieries | |
| Saturday 26th December 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 3-0 | Holker Old Boys | |
| Monday 28th December 1998 | |||
|---|---|---|---|
| Premier Division | |||
| Vauxhall GM | 2-1 | Workington | |
| Saturday 2nd January 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 4-0 | Bootle | |
| Saturday 23rd January 1999 | |||
|---|---|---|---|
| F.A. Carlsberg Vase 4th Round | |||
| Oldbury United | 0-4 | Workington | |
| Saturday 6th February 1999 | |||
|---|---|---|---|
| F.A. Carlsberg Vase 5th Round | |||
| Workington | 3-0 | Sudbury Wanderers | |
| (After Extra Time, 0-0 after 90 mins) | |||
| Premier Division | |||
|---|---|---|---|
| Newcastle Town | 1-1 | Workington | |
| Saturday 13th February 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 3-1 | Prescot Cables | |
| Saturday 20th February 1999 | |||
|---|---|---|---|
| F.A. Carlsberg Vase Quarter Finals | |||
| Bedlington Terriers | 1-0 | Workington | |
| (After Extra Time, 0-0 after 90 mins) | |||
| Saturday 27th February 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Kidsgrove Athletic | 2-0 | Workington | |
| Saturday 6th March 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 3-2 | Ramsbottom United | |
| Saturday 13th March 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 4-1 | Atherton LR | |
| Saturday 20th March 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Atherton LR | 1-2 | Workington | |
| Saturday 27th March 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 2-0 | Maine Road | |
| Saturday 3rd April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| St Helens Town | 0-4 | Workington | |
| Monday 5th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Holker Old Boys | 0-2 | Workington | |
| Saturday 10th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 5-0 | Salford City | |
| Monday 12th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Clitheroe | 0-1 | Workington | |
| Saturday 17th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 6-1 | Cheadle Town | |
| Tuesday 20th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 4-0 | Rossendale United | |
| Saturday 24th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Glossop North End | 0-3 | Workington | |
| Tuesday 27th April 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Atherton Collieries | 0-2 | Workington | |
| Saturday 1st May 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 4-2 | St Helens Town | |
| Monday 3rd May 1999 | |||
|---|---|---|---|
| Premier Division | |||
| Workington | 2-1 | Mossley | |
