FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 | | Guisborough Town | – | Atherton Collieries | | 0:4 (0:2) |
| Guisborough |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Guisborough Town | – | Bishop Auckland | | 0:1 (0:0) |
| Guisborough |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | North Shields | – | Guisborough Town | | 2:0 (1:0) |
| North Shields |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Guisborough Town | – | Tadcaster Albion | | 1:2 |
| Guisborough |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Seaham Red Star | – | Guisborough Town | | 3:1 (0:0) |
| Seaham |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Guisborough Town | – | Farsley Celtic | | 0:4 (0:1) |
| Guisborough |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Guisborough Town | – | Shildon | | 1:5 (1:1) |
| Guisborough |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Guisborough Town | – | Bridlington Town | | 2:3 |
| Guisborough |
FA Cup 2015/16, First Qualifying Round |
| 16.09.2015 | | Guisborough Town | – | Ashton United | | 2:3 (1:2) * |
| Guisborough |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Guisborough Town | – | Workington | | 1:4 (1:1) |
| Guisborough |
FA Cup 2012/13, Preliminary Round |
| 29.08.2012 | | Guisborough Town | – | Shildon | | 0:6 * |
| Guisborough |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Guisborough Town | – | Shildon | | 0:1 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Guisborough Town | – | Armthorpe Welfare | | 0:3 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Kendal Town | – | Guisborough Town | | 9:1 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Bridlington Town | – | Guisborough Town | | 3:2 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Guisborough Town | – | Norton & Stockton Ancients | | 1:3 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Guisborough Town | – | Hallam | | 0:3 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Guisborough Town | – | Brigg Town | | 1:3 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Stalybridge Celtic | – | Guisborough Town | | 3:1 * |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Guiseley | – | Guisborough Town | | 1:0 * |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Rossendale United | – | Guisborough Town | | 3:2 |
| |
FA Cup 2000/01, Extra Preliminary Round |
| | | Chadderton | – | Guisborough Town | | 4:1 * |
| |
FA Cup 1999/00, Preliminary Round |
| | | Guisborough Town | – | Farsley Celtic | | 0:1 * |
| |
FA Cup 1998/99, Preliminary Round |
| | | Guisborough Town | – | Rossington Main | | 1:3 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Guisborough Town | – | Worksop Town | | 2:3 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Burton Albion | – | Guisborough Town | | 1:0 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Durham City | – | Guisborough Town | | 2:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Guisborough Town | – | Murton | | 3:4 * |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Barrow | – | Guisborough Town | | 3:1 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Netherfield | – | Guisborough Town | | 4:1 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Dunston Federation Brewery | – | Guisborough Town | | 1:0 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Guisborough Town | – | Gretna | | 1:3 * |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Billingham Synthonia | – | Guisborough Town | | 2:0 |
| |
FA Cup 1988/89, First Round Proper |
| 19.11.1988 | | Guisborough Town | – | Bury | | 0:1 (0:1) |
| |
FA Cup 1987/88, Fourth Qualifying Round |
| | | Guisborough Town | – | Bishop Auckland | | 1:2 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Alnwick Town | – | Guisborough Town | | 1:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Newcastle Blue Star | – | Guisborough Town | | 2:1 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Tow Law Town | – | Guisborough Town | | 4:3 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Guisborough Town | – | Brandon United | | 1:2 * |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Chester-le-Street Town | – | Guisborough Town | | 3:0 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Guisborough Town | – | Seaham Red Star | | 2:3 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Guisborough Town | – | Gateshead | | 2:3 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Tow Law Town | – | Guisborough Town | | 1:0 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Consett | – | Guisborough Town | | 3:2 * |
| |
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