FA Cup 2022/23, Extra Preliminary Round |
 | 09.08.2022 | | Widnes | – | Winsford United | | 2:0 (0:0) * |
| Widnes |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Winsford United | – | Charnock Richard | | 0:2 (0:1) |
| Winsford |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Longridge Town | – | Winsford United | | 2:1 |
| Longridge |
FA Cup 2019/20, Preliminary Round |
| 02.09.2019 | | Winsford United | – | Ramsbottom United | | 1:3 (0:1) * |
| Winsford |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Winsford United | – | Irlam | | 1:2 (1:1) |
| Winsford |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Maine Road | – | Winsford United | | 3:2 |
| Manchester |
FA Cup 2016/17, First Qualifying Round |
| 05.09.2016 | | Winsford United | – | Whitby Town | | 1:2 * |
| Winsford |
FA Cup 2015/16, Extra Preliminary Round |
| 18.08.2015 | | AFC Blackpool | – | Winsford United | | 3:2 (1:1) * |
| Blackpool |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Winsford United | – | Athersley Recreation | | 0:1 |
| Winsford |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Warrington Town | – | Winsford United | | 5:0 (5:0) |
| Warrington |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Winsford United | – | Trafford | | 0:2 |
| Winsford |
FA Cup 2011/12, Extra Preliminary Round |
| 23.08.2011 | | Maine Road | – | Winsford United | | 1:0 * |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Ramsbottom United | – | Winsford United | | 4:1 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 18.08.2009 | | Winsford United | – | Flixton | | 4:6 * |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 19.08.2008 | | Nostell Miners Welfare | – | Winsford United | | 3:0 * |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Winsford United | – | Penrith Town | | 1:3 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Congleton Town | – | Winsford United | | 1:0 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Northallerton Town | – | Winsford United | | 4:0 |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Lincoln United | – | Winsford United | | 5:0 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Whitby Town | – | Winsford United | | 3:0 |
| |
FA Cup 2002/03, Extra Preliminary Round |
| | | West Auckland Town | – | Winsford United | | 2:1 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Winsford United | – | Harrogate Railway Athletic | | 1:4 * |
| |
FA Cup 2000/01, Preliminary Round |
| | | Selby Town | – | Winsford United | | 2:0 * |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Gateshead | – | Winsford United | | 3:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Leigh Railway Mechanics Institute | – | Winsford United | | 1:0 |
| |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Chester City | – | Winsford United | | 2:1 (0:1) |
| Chester |
FA Cup 1996/97, Second Qualifying Round |
| | | Winsford United | – | Newcastle Town | | 0:1 |
| |
FA Cup 1995/96, Fourth Qualifying Round |
| | | Winsford United | – | Barrow | | 0:3 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Winsford United | – | Chadderton | | 5:6 * |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Gretna | – | Winsford United | | 5:0 * |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Northwich Victoria | – | Winsford United | | 4:1 |
| |
FA Cup 1991/92, First Round Proper |
| 16.11.1991 | | Wrexham | – | Winsford United | | 5:2 |
| Wrexham |
FA Cup 1990/91, Preliminary Round |
| | | Bootle | – | Winsford United | | 1:0 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Walsall Wood | – | Winsford United | | 2:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Hinckley Athletic | – | Winsford United | | 3:0 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Colwyn Bay | – | Winsford United | | 3:0 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Winsford United | – | Caernarfon Town | | 1:3 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Leek Town | – | Winsford United | | 2:0 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Stalybridge Celtic | – | Winsford United | | 5:0 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Winsford United | – | Eastwood Town | | 0:1 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Winsford United | – | Blakenall | | 1:2 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Winsford United | – | Caernarfon Town | | 2:3 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Winsford United | – | Burton Albion | | 1:3 * |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Winsford United | – | Mossley | | 0:1 |
| |
FA Cup 1978/79, Third Qualifying Round |
| | | Winsford United | – | Hednesford Town | | 1:2 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Mossley | – | Winsford United | | 2:0 * |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Bangor City | – | Winsford United | | 4:1 * |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Peterborough United | – | Winsford United | | 4:1 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Winsford United | – | Marine | | 1:4 * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Winsford United | – | Porthmadog | | 1:2 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Ellesmere Port Town | – | Winsford United | | 1:0 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Eastwood Hanley | – | Winsford United | | 1:0 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Oswestry Town | – | Winsford United | | 1:0 * |
| |
FA Cup 1969/70, First Qualifying Round |
| | | New Brighton | – | Winsford United | | 2:1 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Winsford United | – | Kirkby Town | | 2:4 |
| |
FA Cup 1967/68, Third Qualifying Round |
| | | Runcorn | – | Winsford United | | 7:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Lostock Gralam | – | Winsford United | | 3:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Macclesfield Town | – | Winsford United | | 7:0 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Witton Albion | – | Winsford United | | 2:1 * |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Macclesfield Town | – | Winsford United | | 1:0 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Winsford United | – | Droylsden | | 0:1 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Congleton Town | – | Winsford United | | 3:1 |
| |
FA Cup 1959/60, Preliminary Round |
| | | Winsford United | – | Northwich Victoria | | 0:3 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Winsford United | – | Hyde United | | 1:2 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Macclesfield Town | – | Winsford United | | 5:4 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Macclesfield Town | – | Winsford United | | 4:1 * |
| |
FA Cup 1955/56, Third Qualifying Round |
| | | Winsford United | – | Northwich Victoria | | 1:2 * |
| |
FA Cup 1954/55, Preliminary Round |
| | | Hyde United | – | Winsford United | | 3:1 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Nelson | – | Winsford United | | 1:0 |
| |
FA Cup 1952/53, Third Qualifying Round |
| | | Winsford United | – | Altrincham | | 0:1 |
| |
FA Cup 1951/52, Second Qualifying Round |
| | | Buxton | – | Winsford United | | 4:0 |
| |
FA Cup 1950/51, Second Qualifying Round |
| | | Altrincham | – | Winsford United | | 3:2 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Winsford United | – | Droylsden United | | 2:3 |
| |
FA Cup 1948/49, Third Qualifying Round |
| | | Winsford United | – | Witton Albion | | 0:1 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Ashton United | – | Winsford United | | 2:0 |
| |
FA Cup 1887/88, Second Round |
| 05.11.1887 | | Over Wanderers | – | Stoke | | 0:2 |
| |
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