FA Cup 2021/22, Preliminary Round |
 | 21.08.2021 | | Winterton Rangers | – | Deeping Rangers | | 4:1 (2:0) |
| Winterton |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Winterton Rangers | – | Grimsby Borough | | 6:2 (2:2) |
| Winterton |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Winterton Rangers | – | Grimsby Borough | | 2:1 (2:1) |
| Winterton |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Alsager Town | – | Winterton Rangers | | 2:3 |
| Alsager |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Maltby Main | – | Winterton Rangers | | 0:1 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Greenwood Meadows | – | Winterton Rangers | | 3:4 |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Winterton Rangers | – | St Andrews | | 6:1 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Dunkirk | – | Winterton Rangers | | 1:3 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Winterton Rangers | – | Warrington Town | | 4:2 |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Radcliffe Borough | – | Winterton Rangers | | 1:2 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Barton Town Old Boys | – | Winterton Rangers | | 1:3 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Winterton Rangers | – | Morpeth Town | | 1:0 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Winterton Rangers | – | Armthorpe Welfare | | 3:2 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Winterton Rangers | – | West Auckland Town | | 3:0 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 23.08.2006 | | Winterton Rangers | – | Daisy Hill | | 3:0 * |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Winterton Rangers | – | North Shields | | 1:0 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Winterton Rangers | – | Darwen | | 2:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Winterton Rangers | – | Stocksbridge Park Steels | | 3:0 |
| |
FA Cup 1993/94, Preliminary Round |
| | | Winterton Rangers | – | Prescot | | 2:0 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Winterton Rangers | – | Friar Lane Old Boys | | 1:0 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Winterton Rangers | – | Bourne Town | | 4:3 |
| |
FA Cup 1979/80, Preliminary Round |
| | | Heanor Town | – | Winterton Rangers | | 0:5 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Winterton Rangers | – | Bridlington Trinity | | 2:1 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | North Ferriby United | – | Winterton Rangers | | 0:1 * |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Emley | – | Winterton Rangers | | 4:7 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Winterton Rangers | – | Denaby United | | 2:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Retford Town | – | Winterton Rangers | | 0:3 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Frecheville Community | – | Winterton Rangers | | 0:1 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Winterton Rangers | – | Yorkshire Amateur | | 4:2 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Winterton Rangers | – | Whitby Town | | 3:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Winterton Rangers | – | Barton Town | | 1:0 * |
| |
FA Cup 1972/73, Preliminary Round |
| | | Winterton Rangers | – | Frickley Colliery | | 2:0 |
| |
FA Cup 1971/72, Third Qualifying Round |
| | | Eastwood Town | – | Winterton Rangers | | 1:2 |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Winterton Rangers | – | Lincoln United | | 3:1 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Norton Woodseats | – | Winterton Rangers | | 0:3 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Winterton Rangers | – | Selby Town | | 3:1 |
| |
FA Cup 1969/70, Preliminary Round |
| | | Winterton Rangers | – | Selby Town | | 5:2 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Bentley Colliery | – | Winterton Rangers | | 2:4 |
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