| Saturday 30th August 1986 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Penrith | 6-2 | Glossop | |
| Saturday 4th October 1986 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Workington | 1-1 | Glossop | |
| Tuesday 7th October 1986 | F.A. Trophy 1st Qualifying Round Replay | ||
|---|---|---|---|
| Glossop | 1-0 | Workington | |
| Saturday 1st November 1986 | F.A. Trophy 2nd Qualifying Round | ||
|---|---|---|---|
| Whitley Bay | 2-0 | Glossop | |
