FA Cup 2023/24, Extra Preliminary Round |
 | 09.08.2023 | | Guisborough Town | – | Newton Aycliffe | | 2:2 (0:1) |
| Guisborough |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | North Shields | – | Guisborough Town | | 2:2 (2:0) |
| North Shields |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Albion Sports | – | Guisborough Town | | 2:2 (1:1) |
| Bradford |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Guisborough Town | – | Newton Aycliffe | | 3:3 (2:0) |
| Guisborough |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Ashton United | – | Guisborough Town | | 0:0 |
| Ashton-under-Lyne |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Sunderland RCA | – | Guisborough Town | | 4:4 |
| Sunderland |
FA Cup 2014/15, Extra Preliminary Round |
| 19.08.2014 | | Armthorpe Welfare | – | Guisborough Town | | 2:2 aet
(1:2, 2:2),
pen. 3:2 * |
| Armthorpe |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Guisborough Town | – | Armthorpe Welfare | | 1:1 (1:0) |
| Guisborough |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Jarrow Roofing Boldon CA FC | – | Guisborough Town | | 3:3 |
| Boldon Colliery |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Guisborough Town | – | Bishop Auckland | | 2:2 |
| Guisborough |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Guisborough Town | – | Bridlington Town | | 1:1 |
| Guisborough |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Shildon | – | Guisborough Town | | 1:1 |
| Shildon |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Wakefield | – | Guisborough Town | | 0:0 |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 22.08.2005 | | Great Harwood Town | – | Guisborough Town | | 3:3,
pen. 4:2 * |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Guisborough Town | – | Great Harwood Town | | 1:1 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Guisborough Town | – | Stalybridge Celtic | | 2:2 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Kendal Town | – | Guisborough Town | | 2:2,
pen. 7:8 * |
| |
FA Cup 2003/04, Preliminary Round |
| | | Guisborough Town | – | Kendal Town | | 1:1 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Guisborough Town | – | Guiseley | | 3:3 |
| |
FA Cup 2000/01, Extra Preliminary Round |
| | | Guisborough Town | – | Chadderton | | 1:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Farsley Celtic | – | Guisborough Town | | 1:1 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Louth United | – | Guisborough Town | | 2:2 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Murton | – | Guisborough Town | | 1:1 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Gretna | – | Guisborough Town | | 2:2 |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Leek Town | – | Guisborough Town | | 0:0 |
| |
FA Cup 1988/89, Third Qualifying Round |
| | | Guisborough Town | – | Bridlington Town | | 1:1 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Guisborough Town | – | Farsley Celtic | | 0:0 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Guisborough Town | – | Thackley | | 0:0 aet * |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Thackley | – | Guisborough Town | | 1:1 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Blyth Spartans | – | Guisborough Town | | 1:1 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Brandon United | – | Guisborough Town | | 0:0 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Guisborough Town | – | Chester-le-Street Town | | 0:0 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Guisborough Town | – | Consett | | 2:2 |
| |
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