Saturday 14th August 1999
Premier Division
Cheadle Town	2-0	Atherton LR

 

Thursday 19th August 1999
Premier Division
Nantwich Town	0-2	Cheadle Town

 

Saturday 21st August 1999
F.A. Challenge Cup Preliminary Round
Cheadle Town	0-3	Warrington Town

 

Tuesday 24th August 1999
Premier Division
Cheadle Town	0-0	Leek CSOB

 

Saturday 28th August 1999
Premier Division
Vauxhall Motors	8-0	Cheadle Town

 

Tuesday 31st August 1999
Premier Division
Cheadle Town	1-1	Ramsbottom United

 

Saturday 4th September 1999
Premier Division
Maine Road	2-0	Cheadle Town

 

Tuesday 7th September 1999
Premier Division
Cheadle Town	3-4	Atherton Collieries

 

Saturday 11th September 1999
Premier Division
Prescot Cables	3-1	Cheadle Town

 

Wednesday 15th September 1999
Premier Division
St Helens Town	1-0	Cheadle Town

 

Saturday 18th September 1999
Premier Division
Cheadle Town	1-2	Salford City

 

Saturday 25th September 1999
F.A. Carlsberg Vase 2nd Qualifying Round
Cheadle Town	6-0	Esh Winning

 

Saturday 2nd October 1999
Premier Division
Kidsgrove Athletic	6-0	Cheadle Town

 

Tuesday 5th October 1999
Premier Division
Ramsbottom United	4-1	Cheadle Town

 

Saturday 9th October 1999
Premier Division
Cheadle Town	4-2	Glossop North End

 

Tuesday 12th October 1999
Premier Division
Cheadle Town	1-1	St Helens Town

 

Saturday 16th October 1999
Premier Division
Great Harwood Town	2-2	Cheadle Town

 

Tuesday 19th October 1999
Premier Division
Mossley	2-2	Cheadle Town

 

Saturday 23rd October 1999
F.A. Carlsberg Vase 1st Round
Crook Town	3-1	Cheadle Town

 

Tuesday 26th October 1999
Premier Division
Cheadle Town	0-1	Great Harwood Town

 

Saturday 30th October 1999
Premier Division
Leek CSOB	4-5	Cheadle Town

 

Saturday 6th November 1999
Premier Division
Clitheroe	4-2	Cheadle Town

 

Tuesday 9th November 1999
Premier Division
Rossendale United	4-2	Cheadle Town

 

Saturday 20th November 1999
Premier Division
Cheadle Town	1-1	Newcastle Town

 

Tuesday 30th November 1999
Premier Division
Cheadle Town	2-2	Maine Road

 

Saturday 18th December 1999
Premier Division
Bootle	0-0	Cheadle Town

 

Monday 27th December 1999
Premier Division
Abbey Hey	0-2	Cheadle Town

 

Monday 3rd January 2000
Premier Division
Cheadle Town	0-1	Abbey Hey

 

Saturday 8th January 2000
Premier Division
Salford City	1-1	Cheadle Town

 

Saturday 15th January 2000
Premier Division
Cheadle Town	0-0	Mossley

 

Saturday 22nd January 2000
Premier Division
Cheadle Town	1-0	Nantwich Town

 

Saturday 29th January 2000
Premier Division
Cheadle Town	0-2	Fleetwood Freeport

 

Saturday 12th February 2000
Premier Division
Glossop North End	1-0	Cheadle Town

 

Saturday 19th February 2000
Premier Division
Cheadle Town	0-1	Clitheroe

 

Saturday 26th February 2000
Premier Division
Cheadle Town	3-0	Kidsgrove Athletic

 

Tuesday 29th February 2000
Premier Division
Newcastle Town	4-1	Cheadle Town

 

Saturday 4th March 2000
Premier Division
Fleetwood Freeport	0-0	Cheadle Town

 

Saturday 11th March 2000
Premier Division
Atherton LR	1-1	Cheadle Town

 

Saturday 18th March 2000
Premier Division
Cheadle Town	1-0	Bootle

 

Saturday 25th March 2000
Premier Division
Cheadle Town	1-2	Skelmersdale United

 

Saturday 1st April 2000
Premier Division
Cheadle Town	1-3	Vauxhall Motors

 

Tuesday 4th April 2000
Premier Division
Skelmersdale United	3-0	Cheadle Town

 

Tuesday 11th April 2000
Premier Division
Cheadle Town	1-5	Prescot Cables

 

Saturday 22nd April 2000
Premier Division
Atherton Collieries	4-1	Cheadle Town

 

Wednesday 26th April 2000
Premier Division
Cheadle Town	3-3	Rossendale United