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 2018/19, Preliminary Round |
| 25.08.2018 | | Pickering Town | – | Colne | | 0:4 (0:1) |
| Pickering |
FA Cup 2017/18, Preliminary Round |
| 20.08.2017 | | Pickering Town | – | Clitheroe | | 1:2 (0:1) |
| Pickering |
FA Cup 2016/17, Preliminary Round |
| 23.08.2016 | | Pickering Town | – | Washington | | 1:2 * |
| Pickering |
FA Cup 2015/16, Preliminary Round |
| 30.08.2015 | | Pickering Town | – | Clitheroe | | 1:5 (0:3) |
| 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 2011/12, First Qualifying Round |
| 21.09.2011 | | Staveley Miners Welfare | – | Pickering Town | | 4:0 * |
| Staveley |
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 2007/08, Preliminary Round |
| 01.09.2007 | | Selby Town | – | Pickering Town | | 4:0 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Pickering Town | – | New Mills | | 0:1 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Pickering Town | – | Farsley Celtic | | 1:2 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Gateshead | – | Pickering Town | | 2:0 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Pickering Town | – | Ossett Albion | | 0:1 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Pickering Town | – | Matlock Town | | 0:1 * |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Pickering Town | – | Accrington Stanley | | 1:2 |
| |
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 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 1995/96, First Qualifying Round |
| | | Lancaster City | – | Pickering Town | | 2:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Tow Law Town | – | Pickering Town | | 4:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Pickering Town | – | Northallerton Town | | 0:2 |
| |
