| Saturday 30th August 1986 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Bootle | 2-0 | Belper Town | |
| Saturday 13th September 1986 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Burscough | 2-2 | Bootle | |
| Tuesday 16th September 1986 | F.A. Challenge Cup 1st Qualifying Round Replay | ||
|---|---|---|---|
| Bootle | 2-1 | Burscough | |
| Saturday 27th September 1986 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Bootle | 2-2 | Eastwood Town | |
| Tuesday 30th September 1986 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Eastwood Town | 1-1 | Bootle | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Saturday 4th October 1986 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Bootle | 3-0 | Penrith | |
| Monday 6th October 1986 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Bootle | 1-1 | Eastwood Town | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Wednesday 8th October 1986 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Eastwood Town | 1-0 | Bootle | |
| Saturday 1st November 1986 | F.A. Trophy 2nd Qualifying Round | ||
|---|---|---|---|
| Bootle | 2-5 | Newcastle Blue Star | |
