FA Cup 2019/20, Extra Preliminary Round |
 | 10.08.2019 |  | Vauxhall Motors | – | Winsford United | | 1:2 (0:0) |
| Ellesmere Port |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Alsager Town | – | Winsford United | | 1:6 |
| Alsager |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Staveley Miners Welfare | – | Winsford United | | 1:2 |
| Staveley |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Stockport Sports | – | Winsford United | | 1:2 |
| Stockport |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Nostell Miners Welfare | – | Winsford United | | 0:1 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Chadderton | – | Winsford United | | 3:4 |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 23.08.2005 | | Alsager Town | – | Winsford United | | 0:1 * |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Witton Albion | – | Winsford United | | 0:1 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Winsford United | – | Morpeth Town | | 2:1 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Winsford United | – | Marske United | | 2:1 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Tadcaster Albion | – | Winsford United | | 0:4 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Glasshoughton Welfare | – | Winsford United | | 0:2 |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Winsford United | – | Penrith | | 2:0 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Whitby Town | – | Winsford United | | 1:4 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Winsford United | – | Leek Town | | 1:0 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Easington Colliery | – | Winsford United | | 2:7 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Winsford United | – | Hinckley Athletic | | 3:2 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Winsford United | – | Emley | | 2:1 * |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Winsford United | – | Borrowash Victoria | | 1:0 |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Winsford United | – | Buxton | | 6:1 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Winsford United | – | Guiseley | | 2:1 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Winsford United | – | Ossett Town | | 3:1 * |
| |
FA Cup 1991/92, Fourth Qualifying Round |
| | | Winsford United | – | Altrincham | | 3:2 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Winsford United | – | Droylsden | | 3:2 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Winsford United | – | Mossley | | 6:0 * |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Winsford United | – | Nantwich Town | | 3:0 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Lancaster City | – | Winsford United | | 1:5 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Winsford United | – | Droylsden | | 2:0 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Winsford United | – | Horwich Railway Mechanics Institute | | 2:1 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Winsford United | – | North Ferriby United | | 3:1 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Winsford United | – | Shepshed Charterhouse | | 3:1 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Winsford United | – | Matlock Town | | 2:1 * |
| |
FA Cup 1981/82, Preliminary Round |
| |  | Rhyl | – | Winsford United | | 0:1 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Winsford United | – | Belper Town | | 5:0 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Winsford United | – | Bilston | | 4:2 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Walsall Wood | – | Winsford United | | 0:3 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Winsford United | – | Glossop | | 2:0 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Winsford United | – | South Liverpool | | 3:1 * |
| |
FA Cup 1979/80, Preliminary Round |
| | | Rhyl | – | Winsford United | | 1:5 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Oswestry Town | – | Winsford United | | 0:1 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Winsford United | – | Mexborough Town | | 3:0 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | New Brighton | – | Winsford United | | 1:3 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Glossop | – | Winsford United | | 0:2 |
| |
FA Cup 1977/78, Preliminary Round |
| | | Ashton United | – | Winsford United | | 0:2 * |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Winsford United | – | Runcorn | | 1:0 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Burscough | – | Winsford United | | 1:3 * |
| |
FA Cup 1976/77, Preliminary Round |
| | | South Liverpool | – | Winsford United | | 0:4 |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Winsford United | – | Telford United | | 5:4 * |
| |
FA Cup 1975/76, Third Qualifying Round |
| | | Winsford United | – | Chorley | | 2:0 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Winsford United | – | Witton Albion | | 3:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Winsford United | – | New Brighton | | 4:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Winsford United | – | Prescot Town | | 5:1 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Winsford United | – | Prescot Town | | 1:0 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Winsford United | – | Northwich Victoria | | 3:1 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Runcorn | – | Winsford United | | 0:2 |
| |
FA Cup 1969/70, Preliminary Round |
| | | Congleton Town | – | Winsford United | | 0:6 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Congleton Town | – | Winsford United | | 0:1 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Winsford United | – | Kirkby Town | | 3:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Winsford United | – | Northwich Victoria | | 1:0 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Winsford United | – | Congleton Town | | 2:1 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Lostock Gralam | – | Winsford United | | 0:3 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Winsford United | – | Witton Albion | | 3:0 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Winsford United | – | Witton Albion | | 1:0 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Winsford United | – | Stalybridge Celtic | | 5:1 * |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Winsford United | – | Linotype & Machinery | | 2:1 * |
| |
FA Cup 1956/57, Preliminary Round |
| | | Stockton Heath | – | Winsford United | | 4:5 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Winsford United | – | Buxton | | 5:1 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Winsford United | – | Stalybridge Celtic | | 6:0 * |
| |
FA Cup 1955/56, Preliminary Round |
| | | Winsford United | – | Witton Albion | | 4:1 |
| |
FA Cup 1953/54, Third Qualifying Round |
| | | Winsford United | – | Altrincham | | 3:1 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Winsford United | – | Congleton Town | | 1:0 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Winsford United | – | Northwich Victoria | | 2:0 * |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Winsford United | – | Macclesfield Town | | 1:0 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Winsford United | – | Northwich Victoria | | 4:2 * |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Winsford United | – | Altrincham | | 2:0 |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Winsford United | – | Congleton Town | | 4:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Winsford United | – | Ashton United | | 2:0 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Winsford United | – | Wheelock Albion | | 9:1 |
| |
FA Cup 1948/49, Second Qualifying Round |
| | | Winsford United | – | Hyde United | | 4:0 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Winsford United | – | Congleton Town | | 2:0 * |
| |
FA Cup 1948/49, Preliminary Round |
| | | Winsford United | – | Glossop | | 3:1 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Over Wanderers | – | Wellington St George's | | 3:1 |
| |
