Saturday 14th August 1999
First Division
Castleton Gabriels	1-0	Bacup Borough

 

Tuesday 17th August 1999
First Division
Castleton Gabriels	2-3	Aylestone Park

 

Saturday 21st August 1999
First Division
Colne	0-1	Castleton Gabriels

 

Tuesday 24th August 1999
First Division
Castleton Gabriels	4-1	Ashton Town

 

Saturday 28th August 1999
First Division
Blackpool Mechanics	0-2	Castleton Gabriels

 

Monday 30th August 1999
First Division
Warrington Town	2-0	Castleton Gabriels

 

Saturday 4th September 1999
First Division
Castleton Gabriels	3-1	Daisy Hill

 

Tuesday 7th September 1999
First Division
Oldham Town	1-2	Castleton Gabriels

 

Saturday 11th September 1999
First Division
Holker Old Boys	2-5	Castleton Gabriels

 

Tuesday 14th September 1999
First Division
Castleton Gabriels	3-0	Tetley Walker

 

Saturday 18th September 1999
First Division
Castleton Gabriels	0-0	Nelson

 

Tuesday 21st September 1999
First Division
Castleton Gabriels	4-2	Formby

 

Saturday 25th September 1999
F.A. Carlsberg Vase 2nd Qualifying Round
Oldham Town	0-3	Castleton Gabriels

 

Saturday 2nd October 1999
First Division
Castleton Gabriels	3-3	Warrington Town

 

Saturday 16th October 1999
First Division
Nelson	4-0	Castleton Gabriels

 

Saturday 23rd October 1999
F.A. Carlsberg Vase 1st Round
Goole AFC	1-0	Castleton Gabriels

 

Tuesday 26th October 1999
First Division
Castleton Gabriels	2-2	Chadderton

 

Saturday 30th October 1999
First Division
Aylestone Park	3-2	Castleton Gabriels

 

Tuesday 2nd November 1999
First Division
Bacup Borough	4-1	Castleton Gabriels

 

Friday 12th November 1999
First Division
Castleton Gabriels	2-1	Holker Old Boys

 

Saturday 20th November 1999
First Division
Ashton Town	0-3	Castleton Gabriels

 

Saturday 27th November 1999
First Division
Castleton Gabriels	1-1	Darwen

 

Monday 27th December 1999
First Division
Curzon Ashton	2-0	Castleton Gabriels

 

Monday 3rd January 2000
First Division
Castleton Gabriels	0-5	Curzon Ashton

 

Saturday 8th January 2000
First Division
Darwen	3-1	Castleton Gabriels

 

Saturday 15th January 2000
First Division
Daisy Hill	0-3	Castleton Gabriels

 

Saturday 22nd January 2000
First Division
Squires Gate	6-0	Castleton Gabriels

 

Saturday 5th February 2000
First Division
Woodley Sports	2-2	Castleton Gabriels

 

Saturday 12th February 2000
First Division
Castleton Gabriels	6-2	Oldham Town

 

Saturday 19th February 2000
First Division
Castleton Gabriels	2-2	Blackpool Mechanics

 

Saturday 26th February 2000
First Division
Chadderton	2-0	Castleton Gabriels

 

Saturday 4th March 2000
First Division
Castleton Gabriels	1-4	Woodley Sports

 

Saturday 11th March 2000
First Division
Castleton Gabriels	4-1	Squires Gate

 

Saturday 18th March 2000
First Division
Tetley Walker	4-2	Castleton Gabriels

 

Saturday 25th March 2000
First Division
Castleton Gabriels	3-0	Colne

 

Saturday 1st April 2000
First Division
Formby	4-2	Castleton Gabriels