| Saturday 13th September 1986 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Winsford United | 2-0 | Droylsden | |
| Saturday 27th September 1986 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Winsford United | 1-3 | Caernarfon Town | |
| Saturday 4th October 1986 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Winsford United | 1-2 | Dudley Town | |
