| Saturday 15th August 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 3-0 | Rossendale United | |
| Wednesday 19th August 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 1-2 | Vauxhall GM | |
| Saturday 22nd August 1998 | Premier Division | ||
|---|---|---|---|
| Holker Old Boys | 1-4 | St Helens Town | |
| Tuesday 25th August 1998 | Premier Division | ||
|---|---|---|---|
| Newcastle Town | 5-0 | St Helens Town | |
| Saturday 29th August 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 2-2 | Ramsbottom United | |
| Monday 31st August 1998 | Premier Division | ||
|---|---|---|---|
| Leek CSOB | 1-3 | St Helens Town | |
| Saturday 12th September 1998 | Premier Division | ||
|---|---|---|---|
| Cheadle Town | 0-5 | St Helens Town | |
| Tuesday 15th September 1998 | Premier Division | ||
|---|---|---|---|
| Kidsgrove Athletic | 2-1 | St Helens Town | |
| Saturday 19th September 1998 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| St Helens Town | 3-1 | Brandon United | |
| Wednesday 23rd September 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 3-0 | Bootle | |
| Saturday 26th September 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 1-2 | Clitheroe | |
| Saturday 3rd October 1998 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Droylsden | 6-0 | St Helens Town | |
| Saturday 10th October 1998 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Hall Road Rangers | 1-2 | St Helens Town | |
| Saturday 17th October 1998 | Premier Division | ||
|---|---|---|---|
| Salford City | 1-3 | St Helens Town | |
| Saturday 31st October 1998 | Premier Division | ||
|---|---|---|---|
| Rossendale United | 1-0 | St Helens Town | |
| Wednesday 4th November 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 3-1 | Maine Road | |
| Saturday 7th November 1998 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| St Helens Town | 2-1 | Brigg Town | |
| Tuesday 10th November 1998 | Premier Division | ||
|---|---|---|---|
| Bootle | 0-4 | St Helens Town | |
| Saturday 14th November 1998 | Premier Division | ||
|---|---|---|---|
| Mossley | 2-1 | St Helens Town | |
| Saturday 21st November 1998 | Premier Division | ||
|---|---|---|---|
| Clitheroe | 1-2 | St Helens Town | |
| Saturday 28th November 1998 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| St Helens Town | 2-2 | Morpeth Town | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Tuesday 1st December 1998 | F.A. Carlsberg Vase | ||
|---|---|---|---|
| Morpeth Town | 0-4 | St Helens Town | |
| Saturday 12th December 1998 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| St Helens Town | 3-1 | Eccleshill United | |
| Saturday 19th December 1998 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 5-0 | Holker Old Boys | |
| Saturday 26th December 1998 | Premier Division | ||
|---|---|---|---|
| Skelmersdale United | 3-2 | St Helens Town | |
| Saturday 2nd January 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 3-2 | Mossley | |
| Saturday 23rd January 1999 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Clitheroe | 1-0 | St Helens Town | |
| Wednesday 27th January 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 4-1 | Cheadle Town | |
| Saturday 30th January 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 1-0 | Glossop North End | |
| Tuesday 16th February 1999 | Premier Division | ||
|---|---|---|---|
| Atherton LR | 0-1 | St Helens Town | |
| Saturday 20th February 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 0-3 | Kidsgrove Athletic | |
| Saturday 13th March 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 3-1 | Nantwich Town | |
| Tuesday 16th March 1999 | Premier Division | ||
|---|---|---|---|
| Nantwich Town | 1-0 | St Helens Town | |
| Saturday 20th March 1999 | Premier Division | ||
|---|---|---|---|
| Maine Road | 0-1 | St Helens Town | |
| Wednesday 24th March 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 2-2 | Salford City | |
| Saturday 27th March 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 0-0 | Newcastle Town | |
| Tuesday 30th March 1999 | Premier Division | ||
|---|---|---|---|
| Prescot Cables | 4-1 | St Helens Town | |
| Saturday 3rd April 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 0-4 | Workington | |
| Monday 5th April 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 0-6 | Skelmersdale United | |
| Thursday 8th April 1999 | Premier Division | ||
|---|---|---|---|
| Glossop North End | 0-1 | St Helens Town | |
| Saturday 10th April 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 4-0 | Leek CSOB | |
| Wednesday 14th April 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 1-0 | Atherton LR | |
| Saturday 17th April 1999 | Premier Division | ||
|---|---|---|---|
| Ramsbottom United | 2-3 | St Helens Town | |
| Saturday 24th April 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 2-2 | Atherton Collieries | |
| Monday 26th April 1999 | Premier Division | ||
|---|---|---|---|
| Vauxhall GM | 1-2 | St Helens Town | |
| Thursday 29th April 1999 | Premier Division | ||
|---|---|---|---|
| Atherton Collieries | 1-3 | St Helens Town | |
| Saturday 1st May 1999 | Premier Division | ||
|---|---|---|---|
| Workington | 4-2 | St Helens Town | |
| Monday 3rd May 1999 | Premier Division | ||
|---|---|---|---|
| St Helens Town | 0-0 | Prescot Cables | |
