| Saturday 15th August 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 2-1 | Ashton Town | |
| Saturday 22nd August 1998 | First Division | ||
|---|---|---|---|
| Castleton Gabriels | 4-3 | Oldham Town | |
| Tuesday 25th August 1998 | First Division | ||
|---|---|---|---|
| Blackpool Mechanics | 4-0 | Oldham Town | |
| Saturday 29th August 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-1 | Nelson | |
| Saturday 5th September 1998 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Oldham Town | 0-2 | Warrington Town | |
| Tuesday 8th September 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-1 | Colne | |
| Saturday 12th September 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-5 | Warrington Town | |
| Saturday 19th September 1998 | First Division | ||
|---|---|---|---|
| Squires Gate | 2-0 | Oldham Town | |
| Tuesday 22nd September 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-1 | Tetley Walker | |
| Tuesday 29th September 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 2-3 | Bacup Borough | |
| Saturday 3rd October 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-6 | Fleetwood Freeport | |
| Saturday 10th October 1998 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Oldham Town | 2-5 | Easington Colliery | |
| Saturday 21st November 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-2 | Castleton Gabriels | |
| Saturday 28th November 1998 | First Division | ||
|---|---|---|---|
| Formby | 4-1 | Oldham Town | |
| Saturday 5th December 1998 | First Division | ||
|---|---|---|---|
| Fleetwood Freeport | 13-0 | Oldham Town | |
| Saturday 12th December 1998 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-2 | Curzon Ashton | |
| Saturday 26th December 1998 | First Division | ||
|---|---|---|---|
| Chadderton | 4-1 | Oldham Town | |
| Saturday 2nd January 1999 | First Division | ||
|---|---|---|---|
| Darwen | 1-0 | Oldham Town | |
| Saturday 30th January 1999 | First Division | ||
|---|---|---|---|
| Curzon Ashton | 1-3 | Oldham Town | |
| Saturday 6th February 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-3 | Squires Gate | |
| Saturday 13th February 1999 | First Division | ||
|---|---|---|---|
| Colne | 3-2 | Oldham Town | |
| Tuesday 23rd February 1999 | First Division | ||
|---|---|---|---|
| Warrington Town | 5-0 | Oldham Town | |
| Saturday 27th February 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-1 | Maghull | |
| Saturday 13th March 1999 | First Division | ||
|---|---|---|---|
| Ashton Town | 0-0 | Oldham Town | |
| Tuesday 16th March 1999 | First Division | ||
|---|---|---|---|
| Woodley Sports | 3-0 | Oldham Town | |
| Saturday 20th March 1999 | First Division | ||
|---|---|---|---|
| Tetley Walker | 5-0 | Oldham Town | |
| Saturday 27th March 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-3 | Darwen | |
| Wednesday 31st March 1999 | First Division | ||
|---|---|---|---|
| Nelson | 1-1 | Oldham Town | |
| Saturday 3rd April 1999 | First Division | ||
|---|---|---|---|
| Abbey Hey | 2-0 | Oldham Town | |
| Monday 5th April 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-0 | Chadderton | |
| Saturday 10th April 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 3-4 | Blackpool Mechanics | |
| Tuesday 13th April 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-2 | Daisy Hill | |
| Saturday 24th April 1999 | First Division | ||
|---|---|---|---|
| Maghull | 2-3 | Oldham Town | |
| Tuesday 27th April 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-4 | Woodley Sports | |
| Saturday 1st May 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 1-3 | Formby | |
| Monday 3rd May 1999 | First Division | ||
|---|---|---|---|
| Daisy Hill | 0-5 | Oldham Town | |
| Wednesday 5th May 1999 | First Division | ||
|---|---|---|---|
| Oldham Town | 0-3 | Abbey Hey | |
| Saturday 8th May 1999 | First Division | ||
|---|---|---|---|
| Bacup Borough | 0-0 | Oldham Town | |
