FA Cup 2022/23, Preliminary Round |
 | 20.08.2022 |  | Sheffield | – | Glossop North End | | 0:1 (0:1) |
| Dronfield |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Glossop North End | – | AFC Emley | | 1:0 (0:0) |
| Glossop |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Glossop North End | – | Widnes | | 3:0 (2:0) |
| Glossop |
FA Cup 2019/20, Preliminary Round |
| 03.09.2019 | | Glossop North End | – | Eccleshill United | | 3:1 (0:0) * |
| Glossop |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Glossop North End | – | Prescot Cables | | 2:1 |
| Glossop |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Maltby Main | – | Glossop North End | | 0:6 |
| Maltby |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Glossop North End | – | AFC Blackpool | | 3:0 |
| Glossop |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Runcorn Town | – | Glossop North End | | 0:1 |
| Runcorn |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Armthorpe Welfare | – | Glossop North End | | 1:4 (0:1) |
| Armthorpe |
FA Cup 2012/13, Extra Preliminary Round |
| 15.08.2012 | | Louth Town | – | Glossop North End | | 1:2 * |
| |
FA Cup 2010/11, Preliminary Round |
| 01.09.2010 | | Glossop North End | – | St Helens Town | | 3:1 * |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 17.08.2010 | | Wigan Robin Park | – | Glossop North End | | 0:1 * |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Rossington Main | – | Glossop North End | | 1:2 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 19.08.2009 | | Glossop North End | – | Formby | | 3:1 * |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Pegasus Juniors | – | Glossop North End | | 1:4 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Glossop North End | – | Eccleshall | | 2:0 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Glossop North End | – | New Mills | | 3:1 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Glossop North End | – | Seaham Red Star | | 2:1 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Glossop North End | – | North Shields | | 2:0 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Glossop North End | – | Boldmere St Michaels | | 1:0 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Bourne Town | – | Glossop North End | | 1:2 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Goole Town | – | Glossop North End | | 0:2 |
| |
FA Cup 1993/94, Preliminary Round |
| | | Glasshoughton Welfare | – | Glossop North End | | 0:2 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Skelmersdale United | – | Glossop | | 0:2 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Glossop | – | Goole Town | | 4:0 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Glossop | – | Witton Albion | | 2:0 * |
| |
FA Cup 1980/81, Preliminary Round |
| | | Formby | – | Glossop | | 0:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | New Mills | – | Glossop | | 1:2 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Glossop | – | Mexborough Town | | 3:2 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Rawmarsh Welfare | – | Glossop | | 0:1 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Harrowby | – | Glossop | | 2:11 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Glossop | – | Everton | | 2:1 |
| |
FA Cup 1908/09, Third Round Proper |
| 20.02.1909 | | Sheffield Wednesday | – | Glossop | | 0:1 |
| |
FA Cup 1908/09, Second Round Proper |
| 09.02.1909 | | Glossop | – | Stockport County | | 1:0 * |
| |
FA Cup 1908/09, First Round Proper |
| 16.01.1909 | | Chesterfield | – | Glossop | | 0:2 |
| |
FA Cup 1902/03, Intermediate Round |
| 13.12.1902 | | Glossop | – | New Brompton | | 2:1 |
| |
FA Cup 1901/02, Intermediate Round |
| 14.12.1901 | | Leicester Fosse | – | Glossop | | 0:1 |
| |
