FA Cup 2010/11, Third Qualifying Round |
 | 09.10.2010 | | Workington | – | Shildon | | 2:1 |
| |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Workington | – | West Auckland Town | | 2:1 |
| |
FA Cup 2009/10, Third Qualifying Round |
| 10.10.2009 | | Workington | – | Radcliffe Borough | | 3:0 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Workington | – | Cammell Laird | | 4:1 |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 27.10.2007 | | Workington | – | Boston United | | 1:0 (0:0) |
| |
FA Cup 2007/08, Third Qualifying Round |
| 13.10.2007 | | Stalybridge Celtic | – | Workington | | 0:5 |
| |
FA Cup 2007/08, Second Qualifying Round |
| 29.09.2007 | | Consett | – | Workington | | 0:2 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 27.09.2005 | | Workington | – | Stalybridge Celtic | | 2:1 * |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Bamber Bridge | – | Workington | | 1:5 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Bishop Auckland | – | Workington | | 1:2 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Workington | – | Stalybridge Celtic | | 3:1 * |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Workington | – | Mossley | | 2:1 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Workington | – | Fleetwood Town | | 1:0 * |
| |
FA Cup 2001/02, Preliminary Round |
| | | Workington | – | Penrith | | 1:0 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Billingham Town | – | Workington | | 0:1 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Workington | – | Crook Town | | 3:1 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Workington | – | Worksop Town | | 1:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Whitley Bay | – | Workington | | 1:2 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Workington | – | Hebburn | | 8:1 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Workington | – | Easington Colliery | | 1:0 * |
| |
FA Cup 1992/93, Preliminary Round |
| | | Workington | – | West Auckland Town | | 3:2 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Murton | – | Workington | | 2:4 * |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Brandon United | – | Workington | | 0:1 * |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Workington | – | Billingham Synthonia | | 2:1 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Penrith | – | Workington | | 0:2 * |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Workington | – | Buxton | | 4:1 |
| |
FA Cup 1980/81, Fourth Qualifying Round |
| | | Workington | – | Bishop Auckland | | 4:1 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Southport | – | Workington | | 1:3 |
| |
FA Cup 1978/79, Fourth Qualifying Round |
| | | Workington | – | Gateshead | | 3:2 * |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Southport | – | Workington | | 1:3 |
| |
FA Cup 1970/71, Second Round Proper |
| 16.12.1970 | | Workington | – | Chesterfield | | 3:2 * |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Scarborough | – | Workington | | 2:3 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Workington | – | Rochdale | | 2:1 (0:0) |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Workington | – | Scunthorpe United | | 2:0 |
| |
FA Cup 1967/68, First Round Proper |
| 09.12.1967 | | Ryhope Colliery Welfare | – | Workington | | 0:1 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | South Shields | – | Workington | | 1:4 |
| |
FA Cup 1964/65, Second Round Proper |
| 05.12.1964 | | South Liverpool | – | Workington | | 0:2 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Workington | – | Rochdale | | 2:0 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Workington | – | Halifax Town | | 4:1 |
| |
FA Cup 1962/63, First Round Proper |
| 08.11.1962 | | Workington | – | North Shields | | 7:2 * |
| |
FA Cup 1961/62, Second Round Proper |
| 25.11.1961 | | Gateshead | – | Workington | | 0:2 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Workington | – | Worksop Town | | 2:0 |
| |
FA Cup 1959/60, Second Round Proper |
| 05.12.1959 | | Workington | – | Halifax Town | | 1:0 |
| |
FA Cup 1959/60, First Round Proper |
| 18.11.1959 | | Workington | – | Southport | | 3:0 * |
| |
FA Cup 1957/58, Second Round Proper |
| 07.12.1957 | | Oldham Athletic | – | Workington | | 1:5 |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | Workington | – | Crook Town | | 8:1 |
| |
FA Cup 1956/57, First Round Proper |
| 21.11.1956 | | Workington | – | Mansfield Town | | 2:1 * |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Workington | – | Scarborough | | 4:2 |
| |
FA Cup 1954/55, Second Round Proper |
| 11.12.1954 | | Leyton Orient | – | Workington | | 0:1 |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | Workington | – | Hyde United | | 5:1 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Workington | – | Ferryhill Athletic | | 3:0 |
| |
FA Cup 1951/52, Second Round Proper |
| 20.12.1951 | | Workington | – | Witton Albion | | 1:0 * |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Blackhall Colliery Welfare | – | Workington | | 2:5 |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Workington | – | Lancaster City | | 2:1 * |
| |
FA Cup 1947/48, First Round Proper |
| 29.11.1947 | | Lincoln City | – | Workington | | 0:2 |
| |
FA Cup 1947/48, Fourth Qualifying Round |
| | | Workington | – | Netherfield | | 2:1 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Netherfield | – | Workington | | 1:3 |
| |
FA Cup 1935/36, Second Round Proper |
| 14.12.1935 | | Workington | – | Kidderminster Harriers | | 5:1 |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | New Brighton | – | Workington | | 1:3 |
| |
FA Cup 1934/35, First Round Proper |
| 24.11.1934 | | Workington | – | Birmingham Corporation Tramways | | 2:0 |
| |
FA Cup 1933/34, Third Round Proper |
| 13.01.1934 | | Workington | – | Gateshead | | 4:1 |
| |
FA Cup 1933/34, Second Round Proper |
| 09.12.1933 | | Workington | – | Newport County | | 3:1 |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | Workington | – | Southport | | 1:0 |
| |
FA Cup 1932/33, First Round Proper |
| 26.11.1932 | | Workington | – | Scunthorpe United | | 5:1 |
| |
