| 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 | |
