Football League Cup 1976/77, First Round |
 | 30.08.1976 | | Workington | – | Stockport County | | 0:2 * |
| |
Football League Cup 1976/77, First Round |
| 18.08.1976 | | Stockport County | – | Workington | | 0:0 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | Workington | – | Stockport County | | 0:0 |
| |
Football League Cup 1975/76, First Round |
| 26.08.1975 | | Workington | – | Oldham Athletic | | 1:3 |
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Football League Cup 1975/76, First Round |
| 18.08.1975 | | Oldham Athletic | – | Workington | | 3:0 |
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Football League Cup 1974/75, First Round |
| 21.08.1974 | | Workington | – | Hartlepool | | 1:2 |
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Football League Cup 1973/74, First Round |
| 28.08.1973 | | Carlisle United | – | Workington | | 2:2 |
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Football League Cup 1972/73, Second round |
| 06.09.1972 | | Workington | – | Sheffield United | | 0:1 |
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Football League Cup 1972/73, First Round |
| 16.08.1972 | | Workington | – | Preston North End | | 1:0 |
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Football League Cup 1971/72, First Round |
| 18.08.1971 | | Blackburn Rovers | – | Workington | | 2:0 |
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Football League Cup 1970/71, Second round |
| 08.09.1970 | | Luton Town | – | Workington | | 3:0 |
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Football League Cup 1970/71, First Round |
| 18.08.1970 | | Workington | – | Barrow | | 2:0 |
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Football League Cup 1969/70, First Round |
| 18.08.1969 | | Barrow | – | Workington | | 3:1 * |
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Football League Cup 1969/70, First Round |
| 13.08.1969 | | Workington | – | Barrow | | 0:0 |
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Football League Cup 1968/69, Third round |
| 25.09.1968 | | Workington | – | Burnley | | 0:1 |
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Football League Cup 1968/69, Second round |
| 04.09.1968 | | Colchester United | – | Workington | | 0:1 |
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Football League Cup 1968/69, First Round |
| 14.08.1968 | | Workington | – | Rochdale | | 2:1 |
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Football League Cup 1967/68, Third round |
| 16.10.1967 | | Fulham | – | Workington | | 6:2 * |
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Football League Cup 1967/68, Third round |
| 11.10.1967 | | Workington | – | Fulham | | 2:2 |
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Football League Cup 1967/68, Second round |
| 13.09.1967 | | Carlisle United | – | Workington | | 0:2 |
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Football League Cup 1967/68, First Round |
| 31.08.1967 | | Workington | – | Oldham Athletic | | 2:1 * |
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Football League Cup 1967/68, First Round |
| 29.08.1967 | | Oldham Athletic | – | Workington | | 1:1 aet * |
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Football League Cup 1967/68, First Round |
| 23.08.1967 | | Workington | – | Oldham Athletic | | 1:1 |
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Football League Cup 1966/67, Third round |
| 05.10.1966 | | Grimsby Town | – | Workington | | 3:0 |
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Football League Cup 1966/67, Second round |
| 14.09.1966 | | Bury | – | Workington | | 2:3 |
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Football League Cup 1966/67, First Round |
| 24.08.1966 | | Southport | – | Workington | | 0:1 |
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Football League Cup 1965/66, Third round |
| 20.10.1965 | | Ipswich Town | – | Workington | | 3:1 * |
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Football League Cup 1965/66, Third round |
| 13.10.1965 | | Workington | – | Ipswich Town | | 1:1 |
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Football League Cup 1965/66, Second round |
| 30.09.1965 | | Brentford | – | Workington | | 1:2 * |
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Football League Cup 1965/66, Second round |
| 22.09.1965 | | Workington | – | Brentford | | 0:0 |
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Football League Cup 1965/66, First Round |
| 01.09.1965 | | Stockport County | – | Workington | | 2:3 |
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Football League Cup 1964/65, Fifth Round |
| 16.12.1964 | | Chelsea | – | Workington | | 2:0 * |
| London |
Football League Cup 1964/65, Fifth Round |
| 25.11.1964 | | Workington | – | Chelsea | | 2:2 |
| |
Football League Cup 1964/65, Fourth Round |
| 04.11.1964 | | Workington | – | Norwich City | | 3:0 |
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Football League Cup 1964/65, Third round |
| 22.10.1964 | | Blackburn Rovers | – | Workington | | 1:5 * |
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Football League Cup 1964/65, Third round |
| 14.10.1964 | | Workington | – | Blackburn Rovers | | 0:0 |
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Football League Cup 1964/65, Second round |
| 23.09.1964 | | Scunthorpe United | – | Workington | | 0:1 |
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Football League Cup 1964/65, First Round |
| 02.09.1964 | | Workington | – | Barrow | | 9:1 |
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Football League Cup 1963/64, Fifth Round |
| 16.12.1963 | | West Ham United | – | Workington | | 6:0 |
| London |
Football League Cup 1963/64, Fourth Round |
| 26.11.1963 | | Workington | – | Colchester United | | 2:1 |
| |
Football League Cup 1963/64, Third round |
| 04.11.1963 | | Workington | – | Huddersfield Town | | 1:0 |
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Football League Cup 1963/64, Second round |
| 25.09.1963 | | Workington | – | Southport | | 3:0 |
| |
Football League Cup 1963/64, First Round |
| 04.09.1963 | | Oldham Athletic | – | Workington | | 3:5 |
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Football League Cup 1962/63, First Round |
| 05.09.1962 | | Barrow | – | Workington | | 3:2 |
| |
Football League Cup 1961/62, Third round |
| 15.11.1961 | | Workington | – | Blackpool | | 0:1 |
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Football League Cup 1961/62, Second round |
| 09.10.1961 | | Barnsley | – | Workington | | 1:3 |
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Football League Cup 1961/62, First Round |
| 13.09.1961 | | Workington | – | Coventry City | | 3:0 |
| |
Football League Cup 1960/61, Second round |
| 24.10.1960 | | Chelsea | – | Workington | | 4:2 |
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