Football League Cup 1972/73, First Round |
| 16.08.1972 | | Workington | | Preston North End | | 1:0 |
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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 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, 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 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, Second round |
| 30.09.1965 | | Brentford | | Workington | | 1:2 * |
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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, 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, 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, Fourth Round |
| 26.11.1963 | | Workington | | Colchester United | | 2:1 |
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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 |
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Football League Cup 1963/64, First Round |
| 04.09.1963 | | Oldham Athletic | | Workington | | 3:5 |
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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 |
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