| Saturday 30th August 1986 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Walsall Wood | 0-1 | Skelmersdale United | |
| Saturday 13th September 1986 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Skelmersdale United | 1-0 | Sutton Town | |
| Saturday 20th September 1986 | F.A. Carlsberg Vase Preliminary Round | ||
|---|---|---|---|
| Skelmersdale United | 3-3 | Flixton | |
| Tuesday 23rd September 1986 | F.A. Carlsberg Vase Preliminary Round Replay | ||
|---|---|---|---|
| Flixton | 3-0 | Skelmersdale United | |
| Saturday 27th September 1986 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Skelmersdale United | 2-1 | Hednesford Town | |
| Saturday 11th October 1986 | F.A. Challenge Cup 3rd Qualifying Round | ||
|---|---|---|---|
| Skelmersdale United | 2-3 | Northwich Victoria | |
