FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 | | Seaham Red Star | – | Pickering Town | | 1:0 (0:0) |
| Seaham |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Heaton Stannington | – | Pickering Town | | 1:0 (1:0) |
| Newcastle upon Tyne |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Marske United | – | Pickering Town | | 7:0 (3:0) |
| Marske-by-the-Sea |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Penrith | – | Pickering Town | | 3:2 |
| Penrith |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | 1874 Northwich | – | Pickering Town | | 2:0 (1:0) |
| Winsford |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Pickering Town | – | Bridlington Town | | 3:1 (0:1) |
| Pickering |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Pickering Town | – | Colne | | 0:4 (0:1) |
| Pickering |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Bishop Auckland | – | Pickering Town | | 0:2 (0:0) |
| Bishop Auckland |
FA Cup 2017/18, Preliminary Round |
| 20.08.2017 | | Pickering Town | – | Clitheroe | | 1:2 (0:1) |
| Pickering |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Billingham Town | – | Pickering Town | | 0:3 (0:1) |
| Billingham |
FA Cup 2016/17, Preliminary Round |
| 23.08.2016 | | Pickering Town | – | Washington | | 1:2 * |
| Pickering |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Washington | – | Pickering Town | | 2:2 |
| Washington |
FA Cup 2016/17, Extra Preliminary Round |
| 09.08.2016 | | Pickering Town | – | Ryhope Colliery Welfare | | 3:3 aet
(2:2),
pen. 2:1 * |
| Pickering |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Ryhope Colliery Welfare | – | Pickering Town | | 2:2 |
| Ryhope |
FA Cup 2015/16, Preliminary Round |
| 30.08.2015 | | Pickering Town | – | Clitheroe | | 1:5 (0:3) |
| Pickering |
FA Cup 2015/16, Extra Preliminary Round |
| 16.08.2015 | | Pickering Town | – | Thornaby | | 4:0 |
| Pickering |
FA Cup 2014/15, Extra Preliminary Round |
| 17.08.2014 | | Pickering Town | – | Washington | | 0:6 |
| Pickering |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Dunston UTS | – | Pickering Town | | 4:1 (1:1) |
| Dunston |
FA Cup 2012/13, Extra Preliminary Round |
| 14.08.2012 | | Pickering Town | – | Jarrow Roofing Boldon CA | | 2:4 * |
| |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Jarrow Roofing Boldon CA | – | Pickering Town | | 1:1 |
| |
FA Cup 2011/12, First Qualifying Round |
| 21.09.2011 | | Staveley Miners Welfare | – | Pickering Town | | 4:0 * |
| Staveley |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Pickering Town | – | Staveley Miners Welfare | | 2:2 (2:0) |
| |
FA Cup 2011/12, Preliminary Round |
| 06.09.2011 | | Pickering Town | – | Liversedge | | 3:3 aet,
pen. 5:4 * |
| |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Liversedge | – | Pickering Town | | 2:2 |
| |
FA Cup 2011/12, Extra Preliminary Round |
| 21.08.2011 | | Pickering Town | – | Dinnington Town | | 2:0 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 15.08.2010 | | Pickering Town | – | South Shields | | 1:4 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Norton & Stockton Ancients | – | Pickering Town | | 3:0 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Pickering Town | – | Whitley Bay | | 0:1 |
| |
FA Cup 2008/09, Preliminary Round |
| 31.08.2008 | | Whickham | – | Pickering Town | | 0:2 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 17.08.2008 | | Pickering Town | – | Liversedge | | 4:1 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Selby Town | – | Pickering Town | | 4:0 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Washington | – | Pickering Town | | 1:3 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Pickering Town | – | New Mills | | 0:1 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 20.08.2006 | | Pickering Town | – | Formby | | 4:0 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Pickering Town | – | Farsley Celtic | | 1:2 |
| |
FA Cup 2005/06, Preliminary Round |
| 30.08.2005 | | Ashington | – | Pickering Town | | 1:2 * |
| |
FA Cup 2005/06, Preliminary Round |
| 26.08.2005 | | Pickering Town | – | Ashington | | 2:2 |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Bacup Borough | – | Pickering Town | | 0:5 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Gateshead | – | Pickering Town | | 2:0 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Pickering Town | – | Bedlington Terriers | | 1:0 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Pickering Town | – | Ossett Albion | | 0:1 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Bishop Auckland | – | Pickering Town | | 0:1 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Pickering Town | – | Whitley Bay | | 2:0 |
| |
FA Cup 2003/04, Extra Preliminary Round |
| | | Brodsworth Miners Welfare | – | Pickering Town | | 0:1 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Pickering Town | – | Matlock Town | | 0:1 * |
| |
FA Cup 2002/03, Preliminary Round |
| | | Matlock Town | – | Pickering Town | | 2:2 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Pickering Town | – | Accrington Stanley | | 1:2 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Pickering Town | – | Crook Town | | 1:0 * |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Crook Town | – | Pickering Town | | 1:1 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Shotton Comrades | – | Pickering Town | | 1:5 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Kendal Town | – | Pickering Town | | 3:1 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Guiseley | – | Pickering Town | | 6:0 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Pickering Town | – | St Helens Town | | 3:2 * |
| |
FA Cup 1999/00, First Qualifying Round |
| | | St Helens Town | – | Pickering Town | | 1:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Pickering Town | – | Horden Colliery Welfare | | 4:1 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Bedlington Terriers | – | Pickering Town | | 11:1 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Skelmersdale United | – | Pickering Town | | 3:2 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Bishop Auckland | – | Pickering Town | | 3:1 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Pontefract Collieries | – | Pickering Town | | 1:2 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Lancaster City | – | Pickering Town | | 2:1 |
| |
FA Cup 1995/96, Preliminary Round |
| | | South Shields | – | Pickering Town | | 3:4 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Tow Law Town | – | Pickering Town | | 4:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Ryhope CA | – | Pickering Town | | 1:5 |
| |
FA Cup 1993/94, Preliminary Round |
| | | Pickering Town | – | Penrith | | 5:2 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Pickering Town | – | Northallerton Town | | 0:2 |
| |
