FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 |  | Prestwich Heys | – | Bootle | | 3:1 (2:0) |
| Prestwich |
FA Cup 2022/23, Preliminary Round |
| 23.08.2022 | | Bootle | – | Congleton Town | | 1:4 (0:0) * |
| Bootle |
FA Cup 2021/22, First Qualifying Round |
| 07.09.2021 | | United of Manchester | – | Bootle | | 3:2 (1:0) * |
| Manchester |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Skelmersdale United | – | Bootle | | 2:1 |
| Skelmersdale |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Eccleshill United | – | Bootle | | 2:1 (1:0) |
| Wrose |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Penistone Church | – | Bootle | | 2:1 (1:1) |
| Penistone |
FA Cup 2017/18, Extra Preliminary Round |
| 06.08.2017 | | Hallam | – | Bootle | | 3:0 (1:0) |
| Sheffield |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Pontefract Collieries | – | Bootle | | 2:1 |
| Pontefract |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Bootle | – | Atherton Collieries | | 0:2 (0:1) |
| Bootle |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Bootle | – | Runcorn Town | | 0:1 |
| Bootle |
FA Cup 2013/14, First Qualifying Round |
| 17.09.2013 | | Bootle | – | Worksop Town | | 0:4 (0:2) * |
| Bootle |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Bootle | – | Bamber Bridge | | 1:2 (1:0) |
| Bootle |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Woodley Sports | – | Bootle | | 3:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Bootle | – | Warrington Town | | 1:2 |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Bootle | – | Woodley Sports | | 1:4 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Buxton | – | Bootle | | 3:1 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Flixton | – | Bootle | | 2:1 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Bootle | – | Bradford Park Avenue | | 2:3 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Bootle | – | Belper Town | | 2:3 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Flixton | – | Bootle | | 2:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Denaby United | – | Bootle | | 3:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Maltby Miners Welfare | – | Bootle | | 1:0 * |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Bootle | – | Stalybridge Celtic | | 1:3 * |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Chadderton | – | Bootle | | 3:0 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Bootle | – | Droylsden | | 1:3 * |
| |
FA Cup 1990/91, Third Qualifying Round |
| | | Chorley | – | Bootle | | 6:2 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Burscough | – | Bootle | | 2:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Bootle | – | Arnold | | 0:1 |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Marine | – | Bootle | | 1:0 * |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Eastwood Town | – | Bootle | | 1:0 * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Bootle | – | Chorley | | 0:1 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Bootle | – | Marine | | 0:2 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Bootle | – | Bangor City |  | 0:1 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Bootle | – | Ashton United | | 0:1 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Prescot Cables | – | Bootle | | 3:1 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Bootle | – | Chorley | | 0:1 |
| |
