| Saturday 1st September 1990 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Bootle | 1-0 | Winsford United | |
| Saturday 15th September 1990 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Ilkeston Town | 2-3 | Bootle | |
| Saturday 29th September 1990 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Bootle | 2-0 | Southport | |
| Saturday 6th October 1990 | F.A. Carlsberg Vase Preliminary Round | ||
|---|---|---|---|
| Bootle | 1-1 | Clitheroe | |
| Tuesday 9th October 1990 | F.A. Carlsberg Vase Preliminary Round Replay | ||
|---|---|---|---|
| Clitheroe | 3-2 | Bootle | |
| Saturday 13th October 1990 | F.A. Challenge Cup 3rd Qualifying Round | ||
|---|---|---|---|
| Chorley | 6-2 | Bootle | |
