FA Cup 2023/24, Preliminary Round |
 | 19.08.2023 |  | Pontefract Collieries | – | Guisborough Town | | 1:3 (1:1) |
| Pontefract |
FA Cup 2023/24, Extra Preliminary Round |
| 15.08.2023 | | Newton Aycliffe | – | Guisborough Town | | 2:3 (2:0) * |
| Newton Aycliffe |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Penrith | – | Guisborough Town | | 1:2 (0:0) |
| Penrith |
FA Cup 2020/21, Extra Preliminary Round |
| 02.09.2020 | | Guisborough Town | – | Newton Aycliffe | | 1:0 |
| Guisborough |
FA Cup 2019/20, Extra Preliminary Round |
| 14.08.2019 | | Guisborough Town | – | North Shields | | 1:0 (0:0) * |
| Guisborough |
FA Cup 2018/19, Preliminary Round |
| 29.08.2018 | | Guisborough Town | – | Albion Sports | | 4:0 (1:0) * |
| Guisborough |
FA Cup 2018/19, Extra Preliminary Round |
| 14.08.2018 | | Newton Aycliffe | – | Guisborough Town | | 0:2 (0:0) * |
| Newton Aycliffe |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Guisborough Town | – | Stockton Town | | 4:2 |
| Guisborough |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Liversedge | – | Guisborough Town | | 2:5 |
| Cleckheaton |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Guisborough Town | – | Newcastle Benfield | | 4:2 |
| Guisborough |
FA Cup 2015/16, Extra Preliminary Round |
| 19.08.2015 | | Guisborough Town | – | Sunderland RCA | | 3:2 * |
| Guisborough |
FA Cup 2013/14, Second Qualifying Round |
| 02.10.2013 | | Guisborough Town | – | Jarrow Roofing Boldon CA FC | | 3:1 * |
| Guisborough |
FA Cup 2013/14, First Qualifying Round |
| 17.09.2013 | | Bishop Auckland | – | Guisborough Town | | 0:2 * |
| Bishop Auckland |
FA Cup 2013/14, Preliminary Round |
| 04.09.2013 | | Bridlington Town | – | Guisborough Town | | 2:4 * |
| Bridlington |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Thackley | – | Guisborough Town | | 1:3 (1:1) |
| Bradford |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Northallerton Town | – | Guisborough Town | | 4:5 |
| |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Jarrow Roofing Boldon CA | – | Guisborough Town | | 1:2 |
| |
FA Cup 2009/10, Preliminary Round |
| 02.09.2009 | | Guisborough Town | – | Wakefield | | 1:0 * |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 16.08.2009 | | Scarborough Athletic | – | Guisborough Town | | 1:2 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Thornaby | – | Guisborough Town | | 1:2 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Morpeth Town | – | Guisborough Town | | 0:1 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Guisborough Town | – | Blackpool Mechanics | | 2:0 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Guisborough Town | – | Bacup Borough | | 1:0 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Guisborough Town | – | Louth United | | 4:1 * |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Guisborough Town | – | Murton | | 1:0 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Guisborough Town | – | Gretna |  | 1:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Guisborough Town | – | Eppleton Colliery Welfare | | 2:0 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Guisborough Town | – | Billingham Town | | 3:0 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Murton | – | Guisborough Town | | 1:2 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Billingham Town | – | Guisborough Town | | 1:2 |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Guisborough Town | – | Leek Town | | 1:0 * |
| |
FA Cup 1988/89, Third Qualifying Round |
| | | Bridlington Town | – | Guisborough Town | | 0:1 * |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Farsley Celtic | – | Guisborough Town | | 0:1 * |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Guisborough Town | – | Alnwick Town | | 3:0 |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Guisborough Town | – | Emley | | 3:2 |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Rossendale United | – | Guisborough Town | | 2:3 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Guisborough Town | – | Thackley | | 1:0 * |
| |
FA Cup 1987/88, Preliminary Round |
| | | Guisborough Town | – | Armthorpe Welfare | | 2:0 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Guisborough Town | – | Blyth Spartans | | 3:1 * |
| |
FA Cup 1984/85, Preliminary Round |
| | | Esh Winning | – | Guisborough Town | | 0:1 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Guisborough Town | – | Ferryhill Athletic | | 2:1 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Guisborough Town | – | Shildon | | 3:1 |
| |
FA Cup 1979/80, Preliminary Round |
| | | Guisborough Town | – | Newcastle Blue Star | | 3:2 |
| |
