| Saturday 19th September 1998 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| St Helens Town | 3-1 | Brandon United | |
| 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 7th November 1998 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| St Helens Town | 2-1 | Brigg 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 23rd January 1999 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Clitheroe | 1-0 | St Helens Town | |
