| Saturday 26th August 1995 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| St Helens Town | 1-2 | Bootle | |
| Saturday 9th September 1995 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Denaby United | 3-0 | Bootle | |
| Saturday 30th September 1995 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Bootle | 2-1 | Grove United | |
| Saturday 28th October 1995 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Clitheroe | 5-1 | Bootle | |
