| Saturday 29th August 1987 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| St Helens Town | 6-2 | Curzon Ashton | |
| Saturday 12th September 1987 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Ilkeston Town | 1-1 | St Helens Town | |
| Tuesday 15th September 1987 | F.A. Challenge Cup 1st Qualifying Round Replay | ||
|---|---|---|---|
| St Helens Town | 1-1 | Ilkeston Town | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Monday 21st September 1987 | F.A. Challenge Cup 1st Qualifying Round Replay | ||
|---|---|---|---|
| Ilkeston Town | 1-4 | St Helens Town | |
| Saturday 26th September 1987 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| St Helens Town | 0-0 | Horwich RMI | |
| Tuesday 29th September 1987 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Horwich RMI | 2-3 | St Helens Town | |
| Saturday 10th October 1987 | F.A. Challenge Cup 3rd Qualifying Round | ||
|---|---|---|---|
| Northwich Victoria | 3-2 | St Helens Town | |
| Saturday 7th November 1987 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Rainworth Miners Welfare | 1-1 | St Helens Town | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Saturday 14th November 1987 | F.A. Carlsberg Vase 2nd Round Replay | ||
|---|---|---|---|
| St Helens Town | 0-2 | Rainworth Miners Welfare | |
