| Saturday 2nd September 1989 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Brigg Town | 0-2 | St Helens Town | |
| Saturday 16th September 1989 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| St Helens Town | 0-1 | Sandwell Borough | |
| Saturday 4th November 1989 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| St Helens Town | 4-2 | Chadderton | |
| Saturday 25th November 1989 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| St Helens Town | 2-0 | Heswall | |
| Saturday 16th December 1989 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| Darwen | 1-2 | St Helens Town | |
| Saturday 20th January 1990 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Farsley Celtic | 1-1 | St Helens Town | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Wednesday 24th January 1990 | F.A. Carlsberg Vase 4th Round Replay | ||
|---|---|---|---|
| St Helens Town | 0-0 | Farsley Celtic | |
| (After Extra Time, 0-0 after 90 mins) | |||
| Monday 29th January 1990 | F.A. Carlsberg Vase | ||
|---|---|---|---|
| St Helens Town | 0-1 | Farsley Celtic | |
