| Saturday 5th September 1987 | F.A. Carlsberg Vase Extra Preliminary Round | ||
|---|---|---|---|
| Maghull | 0-2 | Bootle | |
| Saturday 12th September 1987 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Bootle | 1-0 | Ashton United | |
| Saturday 19th September 1987 | F.A. Carlsberg Vase Preliminary Round | ||
|---|---|---|---|
| Ford Motors | 1-2 | Bootle | |
| Saturday 26th September 1987 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Bootle | 2-2 | Marine | |
| Tuesday 29th September 1987 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Marine | 1-0 | Bootle | |
| Saturday 17th October 1987 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Bootle | 4-3 | Christleton | |
| Saturday 7th November 1987 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Wythenshawe Amateurs | 2-0 | Bootle | |
