| Saturday 30th August 1986 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Penrith | 6-2 | Glossop | |
| Saturday 13th September 1986 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Warrington Town | 0-2 | Penrith | |
| Saturday 27th September 1986 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Penrith | 1-2 | Chorley | |
| Saturday 4th October 1986 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Bootle | 3-0 | Penrith | |
