FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 |  | Winterton Rangers | – | Melton Town | | 2:4 (2:1) |
| Winterton |
FA Cup 2022/23, Extra Preliminary Round |
| 10.08.2022 | | Winterton Rangers | – | Shepshed Dynamo | | 1:3 aet
(1:1, 1:1) * |
| Winterton |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Bedworth United | – | Winterton Rangers | | 4:1 (1:1) |
| Bedworth |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Winterton Rangers | – | Kirby Muxloe | | 0:1 (0:0) |
| Winterton |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Winterton Rangers | – | Ossett Albion | | 0:3 |
| Winterton |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Runcorn Town | – | Winterton Rangers | | 7:2 |
| Runcorn |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Winterton Rangers | – | Bacup Borough | | 0:3 |
| |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Staveley Miners Welfare | – | Winterton Rangers | | 3:0 |
| |
FA Cup 2010/11, First Qualifying Round |
| 14.09.2010 | | Radcliffe Olympic | – | Winterton Rangers | | 2:0 * |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Buxton | – | Winterton Rangers | | 2:1 |
| |
FA Cup 2008/09, Second Qualifying Round |
| 01.10.2008 | | Newcastle Benfield | – | Winterton Rangers | | 2:1 aet * |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | West Auckland Town | – | Winterton Rangers | | 3:2 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Winterton Rangers | – | Kendal Town | | 0:5 |
| |
FA Cup 2005/06, Preliminary Round |
| 31.08.2005 | | Winterton Rangers | – | Hebburn Town | | 0:2 * |
| |
FA Cup 2004/05, Extra Preliminary Round |
| | | Goole | – | Winterton Rangers | | 1:0 * |
| |
FA Cup 2003/04, Preliminary Round |
| | | Marske United | – | Winterton Rangers | | 3:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Hyde United | – | Winterton Rangers | | 6:0 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Winterton Rangers | – | Sheffield | | 0:1 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Winterton Rangers | – | Nuneaton Borough | | 1:7 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Winterton Rangers | – | Eastwood Town | | 0:3 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Grantham | – | Winterton Rangers | | 4:0 * |
| |
FA Cup 1981/82, Preliminary Round |
| | | Bridlington Trinity | – | Winterton Rangers | | 3:1 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Winterton Rangers | – | Nantwich Town | | 0:1 * |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Sutton Town | – | Winterton Rangers | | 2:0 |
| |
FA Cup 1978/79, Third Qualifying Round |
| | | Yorkshire Amateur | – | Winterton Rangers | | 1:0 |
| |
FA Cup 1977/78, Preliminary Round |
| | | Winterton Rangers | – | Appleby Frodingham Athletic | | 0:1 |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Droylsden | – | Winterton Rangers | | 3:2 * |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Worksop Town | – | Winterton Rangers | | 4:3 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Winterton Rangers | – | Bridlington Town | | 0:2 * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Goole Town | – | Winterton Rangers | | 2:0 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Winterton Rangers | – | Gainsborough Trinity | | 1:3 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Winterton Rangers | – | Boston United | | 0:3 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Winterton Rangers | – | Scarborough | | 1:2 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Hull Brunswick | – | Winterton Rangers | | 2:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Winterton Rangers | – | Ossett Town | | 1:3 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Winterton Rangers | – | Ashby Institute | | 1:4 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Brigg Town | – | Winterton Rangers | | 3:2 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Winterton Rangers | – | Denaby United | | 1:2 |
| |
