FA Cup 2022/23, Extra Preliminary Round |
 | 06.08.2022 |  | Winsford United | – | Widnes | | 1:1 (0:1) |
| Winsford |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Ramsbottom United | – | Winsford United | | 3:3 (3:2) |
| Ramsbottom |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Whitby Town | – | Winsford United | | 3:3 |
| Whitby |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Winsford United | – | AFC Blackpool | | 1:1 |
| Winsford |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Winsford United | – | Maine Road | | 1:1 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Flixton | – | Winsford United | | 3:3 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Winsford United | – | Nostell Miners Welfare | | 3:3 |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Winsford United | – | Alsager Town | | 1:1 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Harrogate Railway Athletic | – | Winsford United | | 1:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Winsford United | – | Selby Town | | 1:1 |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Arnold Town | – | Winsford United | | 0:0,
pen. 6:7 * |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Winsford United | – | Arnold Town | | 1:1 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Emley | – | Winsford United | | 1:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Chadderton | – | Winsford United | | 1:1 |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Winsford United | – | Gretna |  | 0:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Ossett Town | – | Winsford United | | 1:1 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Mossley | – | Winsford United | | 1:1 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | North Ferriby United | – | Winsford United | | 2:2 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Matlock Town | – | Winsford United | | 2:2 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Burton Albion | – | Winsford United | | 2:2 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Belper Town | – | Winsford United | | 2:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | South Liverpool | – | Winsford United | | 2:2 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Mossley | – | Winsford United | | 3:3 aet * |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Winsford United | – | Mossley | | 1:1 |
| |
FA Cup 1977/78, Preliminary Round |
| | | Winsford United | – | Ashton United | | 1:1 |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Winsford United | – | Bangor City |  | 1:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Winsford United | – | Burscough | | 0:0 |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Telford United | – | Winsford United | | 1:1 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Marine | – | Winsford United | | 1:1 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Winsford United | – | Oswestry Town | | 0:0 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Winsford United | – | Witton Albion | | 1:1 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Stalybridge Celtic | – | Winsford United | | 1:1 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Winsford United | – | Macclesfield Town | | 2:2 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Linotype & Machinery | – | Winsford United | | 1:1 |
| |
FA Cup 1955/56, Third Qualifying Round |
| | | Northwich Victoria | – | Winsford United | | 2:2 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Stalybridge Celtic | – | Winsford United | | 1:1 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Winsford United | – | Northwich Victoria | | 1:1 aet * |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Northwich Victoria | – | Winsford United | | 0:0 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Northwich Victoria | – | Winsford United | | 1:1 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Congleton Town | – | Winsford United | | 2:2 |
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