FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Pickering Town | | Bridlington Town | | 3:1 (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, Extra Preliminary Round |
| 05.08.2017 | | Billingham Town | | Pickering Town | | 0:3 (0:1) |
| Billingham |
FA Cup 2015/16, Extra Preliminary Round |
| 16.08.2015 | | Pickering Town | | Thornaby | | 4:0 |
| Pickering |
FA Cup 2011/12, Extra Preliminary Round |
| 21.08.2011 | | Pickering Town | | Dinnington Town | | 2:0 |
| |
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, Extra Preliminary Round |
| 18.08.2007 | | Washington | | Pickering Town | | 1:3 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 20.08.2006 | | Pickering Town | | Formby | | 4:0 |
| |
FA Cup 2005/06, Preliminary Round |
| 30.08.2005 | | Ashington | | Pickering Town | | 1:2 * |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Bacup Borough | | Pickering Town | | 0:5 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Pickering Town | | Bedlington Terriers | | 1:0 |
| |
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 |
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FA Cup 2001/02, First Qualifying Round |
| | | Pickering Town | | Crook Town | | 1:0 * |
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FA Cup 2001/02, Preliminary Round |
| | | Shotton Comrades | | Pickering Town | | 1:5 |
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FA Cup 1999/00, First Qualifying Round |
| | | Pickering Town | | St Helens Town | | 3:2 * |
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FA Cup 1999/00, Preliminary Round |
| | | Pickering Town | | Horden Colliery Welfare | | 4:1 |
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FA Cup 1996/97, Preliminary Round |
| | | Pontefract Collieries | | Pickering Town | | 1:2 |
| |
FA Cup 1995/96, Preliminary Round |
| | | South Shields | | Pickering Town | | 3:4 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Ryhope CA | | Pickering Town | | 1:5 |
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FA Cup 1993/94, Preliminary Round |
| | | Pickering Town | | Penrith | | 5:2 |
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