FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 |  | Glossop North End | – | Colne | | 1:2 (0:1) |
| Glossop |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Liversedge | – | Glossop North End | | 2:1 (2:0) |
| Cleckheaton |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Glossop North End | – | Kendal Town | | 0:1 (0:1) |
| Glossop |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Glossop North End | – | City of Liverpool | | 0:3 |
| Glossop |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Glossop North End | – | Pontefract Collieries | | 1:3 (0:1) |
| Glossop |
FA Cup 2018/19, Preliminary Round |
| 04.09.2018 | | Glossop North End | – | City of Liverpool | | 2:3 aet
(2:2, 2:2) * |
| Glossop |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Glossop North End | – | Mossley AFC | | 0:2 (0:1) |
| Glossop |
FA Cup 2016/17, Preliminary Round |
| 22.08.2016 | | Brighouse Town | – | Glossop North End | | 4:2 * |
| Brighouse |
FA Cup 2015/16, First Qualifying Round |
| 15.09.2015 | | Skelmersdale United | – | Glossop North End | | 2:1 aet
(1:0, 1:1) * |
| Skelmersdale |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Chorley | – | Glossop North End | | 1:0 (0:0) |
| Chorley |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Runcorn Linnets | – | Glossop North End | | 2:1 |
| Runcorn |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Loughborough Dynamo | – | Glossop North End | | 3:0 |
| Loughborough |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Glossop North End | – | Boston Town | | 2:4 |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Glossop North End | – | Mossley | | 0:4 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Glossop North End | – | Chorley | | 2:3 |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Glossop North End | – | Belper Town | | 1:2 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Malvern Town | – | Glossop North End | | 3:0 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Trafford | – | Glossop North End | | 5:0 |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 21.08.2005 | | Stourbridge | – | Glossop North End | | 3:0 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Glossop North End | – | Ludlow Town | | 2:3 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Spalding United | – | Glossop North End | | 3:0 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Solihull Borough | – | Glossop North End | | 9:0 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Glossop North End | – | Stourbridge | | 0:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Spalding United | – | Glossop North End | | 4:0 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Stafford Rangers | – | Glossop North End | | 2:0 |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Glossop North End | – | Grantham Town | | 2:3 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Glossop North End | – | Belper Town | | 1:2 * |
| |
FA Cup 1996/97, Preliminary Round |
| | | Blakenall | – | Glossop North End | | 3:0 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Glossop North End | – | Nantwich Town | | 1:2 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Glossop North End | – | Eastwood Town | | 3:5 * |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Goole Town | – | Glossop North End | | 1:0 * |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Glossop North End | – | Macclesfield Town | | 0:1 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Newtown | – | Glossop | | 4:2 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Maine Road | – | Glossop | | 1:0 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Glossop | – | Maine Road | | 0:4 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Prescot Cables | – | Glossop | | 1:0 * |
| |
FA Cup 1987/88, Preliminary Round |
| | | Glossop | – | Heanor Town | | 2:3 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Penrith | – | Glossop | | 6:2 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Nantwich Town | – | Glossop | | 1:0 |
| |
FA Cup 1984/85, Preliminary Round |
| | | Appleby Frodingham Athletic | – | Glossop | | 2:0 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Glossop | – | Frickley Athletic | | 2:3 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Glossop | – | Worksop Town | | 2:5 |
| |
FA Cup 1981/82, First Qualifying Round |
| |  | Bangor City | – | Glossop | | 6:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Prescot Cables | – | Glossop | | 2:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Winsford United | – | Glossop | | 2:0 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Buxton | – | Glossop | | 3:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Glossop | – | Winsford United | | 0:2 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Droylsden | – | Glossop | | 3:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Fleetwood | – | Glossop | | 2:0 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Emley | – | Glossop | | 4:1 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Altrincham | – | Glossop | | 3:1 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Macclesfield Town | – | Glossop | | 3:0 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Glossop | – | Worksop Town | | 0:1 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Glossop | – | Altrincham | | 1:4 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Glossop | – | Hyde United | | 1:2 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Winsford United | – | Glossop | | 3:1 |
| |
FA Cup 1946/47, First Qualifying Round |
| | | Glossop | – | Rhyl | | 2:6 |
| |
FA Cup 1945/46, First Qualifying Round |
| | | Witton Albion | – | Glossop | | 8:2 |
| |
FA Cup 1914/15, First Round Proper |
| 09.01.1915 | | Queens Park Rangers | – | Glossop | | 2:1 |
| |
FA Cup 1913/14, Second Round Proper |
| 31.01.1914 | | Glossop | – | Preston North End | | 0:1 |
| |
FA Cup 1912/13, First Round Proper |
| 11.01.1913 | | Crystal Palace | – | Glossop | | 2:0 |
| |
FA Cup 1911/12, First Round Proper |
| 13.01.1912 | | Leeds City | – | Glossop | | 1:0 |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | Middlesbrough | – | Glossop | | 1:0 |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | Bury | – | Glossop | | 2:1 |
| |
FA Cup 1908/09, Fourth Round Proper |
| 10.03.1909 | | Bristol City | – | Glossop | | 1:0 * |
| |
FA Cup 1907/08, First Round Proper |
| 15.01.1908 | | Manchester City | – | Glossop | | 6:0 * |
| |
FA Cup 1906/07, First Round Proper |
| 12.01.1907 | | Brentford | – | Glossop | | 2:1 |
| |
FA Cup 1902/03, First Round Proper |
| 07.02.1903 | | Glossop | – | Stoke | | 2:3 |
| |
FA Cup 1901/02, First Round Proper |
| 25.01.1902 | | Glossop | – | Nottingham Forest | | 1:3 |
| |
FA Cup 1900/01, Intermediate Round |
| 05.01.1901 | | Stoke | – | Glossop | | 1:0 |
| |
FA Cup 1898/99, First Round Proper |
| 28.01.1899 | | Glossop | – | Newcastle United | | 0:1 |
| |
FA Cup 1896/97, First Round Proper |
| 30.01.1897 | | Stoke | – | Glossop North End | | 5:2 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Congleton Town | – | Glossop | | +:- |
| |
