FA Cup 2010/11, Fourth Qualifying Round |
 | 26.10.2010 | | Nuneaton Town | – | Workington | | 1:0 * |
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FA Cup 2009/10, Fourth Qualifying Round |
| 24.10.2009 | | Workington | – | Rushden & Diamonds | | 0:3 (0:1) |
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FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Bury | – | Workington | | 4:1 (1:0) |
| Bury |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Ossett Albion | – | Workington | | 2:1 |
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FA Cup 2005/06, Third Qualifying Round |
| 08.10.2005 | | Burscough | – | Workington | | 2:0 |
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FA Cup 2004/05, Third Qualifying Round |
| | | Vauxhall Motors | – | Workington | | 1:0 (0:0) |
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FA Cup 2003/04, Preliminary Round |
| | | Shildon | – | Workington | | 2:1 |
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FA Cup 2002/03, Third Qualifying Round |
| | | Harrogate Railway Athletic | – | Workington | | 4:0 |
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FA Cup 2001/02, First Qualifying Round |
| | | Whitley Bay | – | Workington | | 1:0 |
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FA Cup 2000/01, Preliminary Round |
| | | Workington | – | Farsley Celtic | | 0:1 |
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FA Cup 1999/00, Preliminary Round |
| | | Workington | – | Burscough | | 1:2 |
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FA Cup 1997/98, First Qualifying Round |
| | | Workington | – | Emley | | 0:3 |
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FA Cup 1996/97, Third Qualifying Round |
| | | Gateshead | – | Workington | | 4:0 |
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FA Cup 1995/96, Second Qualifying Round |
| | | Workington | – | Spennymoor United | | 2:4 |
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FA Cup 1994/95, Preliminary Round |
| | | Workington | – | West Auckland Town | | 1:2 * |
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FA Cup 1993/94, Preliminary Round |
| | | Workington | – | Crook Town | | 0:2 |
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FA Cup 1992/93, Second Qualifying Round |
| | | Blyth Spartans | – | Workington | | 6:0 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Workington | – | Gateshead | | 0:1 |
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FA Cup 1990/91, First Qualifying Round |
| | | Horden Colliery Welfare | – | Workington | | 2:1 * |
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FA Cup 1989/90, Preliminary Round |
| | | Workington | – | Crook Town | | 0:1 * |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Gateshead | – | Workington | | 1:0 * |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Bishop Auckland | – | Workington | | 5:2 |
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FA Cup 1986/87, Third Qualifying Round |
| | | Workington | – | Newcastle Blue Star | | 0:1 * |
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FA Cup 1985/86, First Qualifying Round |
| | | Wingate Durham | – | Workington | | 4:2 |
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FA Cup 1984/85, Fourth Qualifying Round |
| | | Stalybridge Celtic | – | Workington | | 1:0 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Mossley | – | Workington | | 1:0 * |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Workington | – | Doncaster Rovers | | 1:2 |
| |
FA Cup 1981/82, First Round Proper |
| 24.11.1981 | | Huddersfield Town | – | Workington | | 5:0 * |
| |
FA Cup 1980/81, First Round Proper |
| 01.12.1980 | | Carlisle United | – | Workington | | 4:1 * |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Chester | – | Workington | | 5:1 |
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FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Rotherham United | – | Workington | | 3:0 |
| |
FA Cup 1977/78, First Round Proper |
| 26.11.1977 | | Workington | – | Grimsby Town | | 0:2 |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Bury | – | Workington | | 6:0 |
| Bury |
FA Cup 1975/76, First Round Proper |
| 25.11.1975 | | Rochdale | – | Workington | | 2:1 * |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Darlington | – | Workington | | 1:0 |
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FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Bradford City | – | Workington | | 2:0 |
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FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Stockport County | – | Workington | | 1:0 |
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FA Cup 1971/72, Second Round Proper |
| 11.12.1971 | | Workington | – | Bury | | 1:3 |
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FA Cup 1970/71, Third Round Proper |
| 02.01.1971 | | Workington | – | Brentford | | 0:1 |
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FA Cup 1969/70, Second Round Proper |
| 06.12.1969 | | Rotherham United | – | Workington | | 3:0 (2:0) |
| |
FA Cup 1968/69, Second Round Proper |
| 11.12.1968 | | Workington | – | Port Vale | | 1:2 * |
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FA Cup 1967/68, Second Round Proper |
| 10.01.1968 | | Workington | – | Doncaster Rovers | | 1:2 * |
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FA Cup 1966/67, Second Round Proper |
| 11.01.1967 | | Bradford Park Avenue | – | Workington | | 3:1 |
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FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Hartlepools United | – | Workington | | 3:1 |
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FA Cup 1964/65, Third Round Proper |
| 09.01.1965 | | Bolton Wanderers | – | Workington | | 4:1 |
| |
FA Cup 1963/64, Second Round Proper |
| 07.12.1963 | | Port Vale | – | Workington | | 2:1 |
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FA Cup 1962/63, Second Round Proper |
| 24.11.1962 | | Hull City | – | Workington | | 2:0 |
| |
FA Cup 1961/62, Third Round Proper |
| 06.01.1962 | | Workington | – | Nottingham Forest | | 1:2 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Stockport County | – | Workington | | 1:0 |
| |
FA Cup 1959/60, Third Round Proper |
| 09.01.1960 | | Crewe Alexandra | – | Workington | | 2:0 |
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FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Accrington Stanley | – | Workington | | 5:1 |
| |
FA Cup 1957/58, Third Round Proper |
| 04.01.1958 | | Workington | – | Manchester United | | 1:3 |
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FA Cup 1956/57, Second Round Proper |
| 12.12.1956 | | Workington | – | Goole Town | | 0:1 * |
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FA Cup 1955/56, Second Round Proper |
| 10.12.1955 | | Bradford Park Avenue | – | Workington | | 4:3 |
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FA Cup 1954/55, Third Round Proper |
| 08.01.1955 | | Luton Town | – | Workington | | 5:0 |
| |
FA Cup 1953/54, Second Round Proper |
| 12.12.1953 | | Stockport County | – | Workington | | 2:1 |
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FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Chesterfield | – | Workington | | 1:0 |
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FA Cup 1951/52, Third Round Proper |
| 12.01.1952 | | Liverpool | – | Workington | | 1:0 |
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FA Cup 1950/51, Fourth Qualifying Round |
| | | Workington | – | Cleator Moor Celtic | | 0:1 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Netherfield | – | Workington | | 2:0 |
| |
FA Cup 1948/49, First Round Proper |
| 27.11.1948 | | Workington | – | Stockport County | | 0:3 |
| |
FA Cup 1947/48, Second Round Proper |
| 13.12.1947 | | Workington | – | Crewe Alexandra | | 1:2 |
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FA Cup 1946/47, First Round Proper |
| 30.11.1946 | | South Liverpool | – | Workington | | 2:1 |
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FA Cup 1945/46, Fourth Qualifying Round |
| | | Workington | – | Chorley | | 1:2 |
| |
FA Cup 1938/39, First Round Proper |
| 30.11.1938 | | Mansfield Town | – | Workington | | 2:1 * |
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FA Cup 1937/38, First Round Proper |
| 27.11.1937 | | New Brighton | – | Workington | | 5:0 |
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FA Cup 1935/36, Third Round Proper |
| 11.01.1936 | | Bradford Park Avenue | – | Workington | | 3:2 |
| |
FA Cup 1934/35, Second Round Proper |
| 13.12.1934 | | Workington | – | Northampton Town | | 0:1 * |
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FA Cup 1933/34, Fourth Round Proper |
| 27.01.1934 | | Workington | – | Preston North End | | 1:2 |
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FA Cup 1932/33, Second Round Proper |
| 10.12.1932 | | Halifax Town | – | Workington | | 2:1 |
| |
FA Cup 1930/31, First Round Proper |
| 29.11.1930 | | Nelson | – | Workington | | 4:0 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Bradford City | – | Workington | | 6:0 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Workington | – | Crook Town | | 1:2 |
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