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