| Saturday 14th August 1999 | First Division | ||
|---|---|---|---|
| Nelson | 3-0 | Oldham Town | |
| Tuesday 17th August 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-2 | Tetley Walker | |
| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Netherfield Kendal | 3-0 | Oldham Town | |
| Tuesday 24th August 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-2 | Alsager | |
| Saturday 28th August 1999 | First Division | ||
|---|---|---|---|
| Holker Old Boys | 3-2 | Oldham Town | |
| Monday 30th August 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-2 | Ashton Town | |
| Saturday 4th September 1999 | First Division | ||
|---|---|---|---|
| Squires Gate | 3-1 | Oldham Town | |
| Tuesday 7th September 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-2 | Castleton Gabriels | |
| Saturday 11th September 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-4 | Curzon Ashton | |
| Tuesday 14th September 1999 | First Division | ||
|---|---|---|---|
| Darwen | 2-0 | Oldham Town | |
| Saturday 18th September 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-5 | Woodley Sports | |
| Wednesday 22nd September 1999 | First Division | ||
|---|---|---|---|
| Curzon Ashton | 4-1 | Oldham Town | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Oldham Town | 0-3 | Castleton Gabriels | |
| Saturday 2nd October 1999 | First Division | ||
|---|---|---|---|
| Woodley Sports | 1-0 | Oldham Town | |
| Tuesday 5th October 1999 | First Division | ||
|---|---|---|---|
| Warrington Town | 0-0 | Oldham Town | |
| Saturday 9th October 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 5-1 | Holker Old Boys | |
| Saturday 16th October 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 3-1 | Daisy Hill | |
| Tuesday 19th October 1999 | First Division | ||
|---|---|---|---|
| Bacup Borough | 6-0 | Oldham Town | |
| Saturday 23rd October 1999 | First Division | ||
|---|---|---|---|
| Colne | 3-1 | Oldham Town | |
| Saturday 30th October 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-2 | Formby | |
| Saturday 13th November 1999 | First Division | ||
|---|---|---|---|
| Tetley Walker | 3-2 | Oldham Town | |
| Saturday 20th November 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 3-3 | Blackpool Mechanics | |
| Monday 27th December 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 2-2 | Chadderton | |
| Monday 3rd January 2000 | First Division | ||
|---|---|---|---|
| Chadderton | 1-1 | Oldham Town | |
| Saturday 22nd January 2000 | First Division | ||
|---|---|---|---|
| Oldham Town | 2-2 | Bacup Borough | |
| Saturday 5th February 2000 | First Division | ||
|---|---|---|---|
| Ashton Town | 0-2 | Oldham Town | |
| Saturday 12th February 2000 | First Division | ||
|---|---|---|---|
| Castleton Gabriels | 6-2 | Oldham Town | |
| Saturday 11th March 2000 | First Division | ||
|---|---|---|---|
| Formby | 1-1 | Oldham Town | |
| Saturday 18th March 2000 | First Division | ||
|---|---|---|---|
| Alsager | 2-1 | Oldham Town | |
| Saturday 25th March 2000 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-3 | Warrington Town | |
| Saturday 1st April 2000 | First Division | ||
|---|---|---|---|
| Daisy Hill | 1-0 | Oldham Town | |
| Tuesday 4th April 2000 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-2 | Squires Gate | |
| Saturday 8th April 2000 | First Division | ||
|---|---|---|---|
| Oldham Town | 2-6 | Nelson | |
| Tuesday 11th April 2000 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-0 | Colne | |
| Saturday 15th April 2000 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-3 | Darwen | |
| Tuesday 2nd May 2000 | First Division | ||
|---|---|---|---|
| Blackpool Mechanics | 5-3 | Oldham Town | |
