Scottish League Cup 2022/23, Group C |
 | 23.07.2022 | | Dunfermline Athletic | – | Alloa Athletic | | 1:1 (1:0),
pen. 4:5 |
| Dunfermline |
Scottish League Cup 2022/23, Group C |
| 12.07.2022 | | Alloa Athletic | – | East Fife | | 1:1 (1:0),
pen. 6:5 |
| Alloa |
Scottish League Cup 2021/22, Group D |
| 24.07.2021 | | Raith Rovers | – | Alloa Athletic | | 0:0,
pen. 5:4 |
| Kirkcaldy |
Scottish League Cup 2019/20, Group C |
| 16.07.2019 | | Alloa Athletic | – | Elgin City | | 3:3 (0:1),
pen. 5:6 |
| Alloa |
Scottish League Cup 2018/19, Group A |
| 21.07.2018 | | Dundee United | – | Alloa Athletic | | 1:1 (1:0),
pen. 3:4 |
| Dundee |
Scottish League Cup 2017/18, Group D |
| 18.07.2017 | | Alloa Athletic | – | Arbroath | | 1:1 (0:1),
pen. 5:6 |
| Alloa |
Scottish League Cup 2013/14, Second Round |
| 27.08.2013 | | Aberdeen | – | Alloa Athletic | | 0:0 aet,
pen. 6:5 |
| Aberdeen |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Airdrie United | – | Alloa Athletic | | 0:0 aet,
pen. 3:4 |
| Airdrie |
Scottish League Cup 1996, Second Round |
| 13.08.1996 | | Motherwell | – | Alloa Athletic | | 0:0 aet,
pen. 2:4 |
| |
Scottish League Cup 1994, First Round |
| 10.08.1994 | | Arbroath | – | Alloa Athletic | | 1:1 aet,
pen. 2:3 |
| |
Scottish League Cup 1991, First Round |
| 13.08.1991 | | Alloa Athletic | – | Stranraer | | 0:0 aet,
pen. 8:7 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Kilmarnock | – | Alloa Athletic | | 1:1 aet,
pen. 3:2 |
| |
Scottish League Cup 1983/84, Group 1 |
| 26.10.1983 | | Motherwell | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | Alloa Athletic | – | Falkirk | | 2:2 |
| |
Scottish League Cup 1981, Group 6 |
| 26.08.1981 | | Stirling Albion | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1981, Group 6 |
| 12.08.1981 | | Alloa Athletic | – | Falkirk | | 1:1 |
| |
Scottish League Cup 1980, Second Round |
| 30.08.1980 | | Hibernian | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1979, First Round |
| 22.08.1979 | | Alloa Athletic | – | Kilmarnock | | 1:1 aet |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | Alloa Athletic | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1976, Group 8 |
| 21.08.1976 | | Queen of the South | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1974, Group 8 |
| 14.08.1974 | | Cowdenbeath | – | Alloa Athletic | | 0:0 |
| |
Scottish League Cup 1972, Supplementary Round |
| 04.09.1972 | | Alloa Athletic | – | Ayr United | | 0:0 |
| |
Scottish League Cup 1971, Supplementary Round |
| 08.09.1971 | | Alloa Athletic | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1971, Group 9 |
| 25.08.1971 | | Forfar Athletic | – | Alloa Athletic | | 0:0 |
| |
Scottish League Cup 1971, Group 9 |
| 21.08.1971 | | Alloa Athletic | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1971, Group 9 |
| 18.08.1971 | | East Stirlingshire | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1970, Group 6 |
| 12.08.1970 | | Berwick Rangers | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1969, Group 9 |
| 12.08.1969 | | Stenhousemuir | – | Alloa Athletic | | 3:3 |
| |
Scottish League Cup 1968/69, Group 9 |
| 24.08.1968 | | East Stirlingshire | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1967, Group 8 |
| 26.08.1967 | | Arbroath | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1964, Group 9 |
| 12.08.1964 | | Alloa Athletic | – | Cowdenbeath | | 0:0 |
| |
Scottish League Cup 1963, Group 5 |
| 10.08.1963 | | Stirling Albion | – | Alloa Athletic | | 3:3 |
| |
Scottish League Cup 1962, Group 8 |
| 01.09.1962 | | Alloa Athletic | – | Arbroath | | 2:2 |
| |
Scottish League Cup 1962, Group 8 |
| 11.08.1962 | | Stirling Albion | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1961, Group 5 |
| 02.09.1961 | | Alloa Athletic | – | Berwick Rangers | | 4:4 |
| |
Scottish League Cup 1961, Group 5 |
| 16.08.1961 | | Stranraer | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1960, Group 7 |
| 17.08.1960 | | Dumbarton | – | Alloa Athletic | | 0:0 |
| |
Scottish League Cup 1959, Group 8 |
| 29.08.1959 | | Alloa Athletic | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1958, Group 7 |
| 30.08.1958 | | Alloa Athletic | – | Queen's Park | | 2:2 |
| |
Scottish League Cup 1957, Group 9 |
| 14.08.1957 | | Alloa Athletic | – | East Stirlingshire | | 3:3 |
| |
Scottish League Cup 1956, Group 5 |
| 18.08.1956 | | Dumbarton | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1955, Group 5 |
| 03.09.1955 | | Alloa Athletic | – | Hamilton Academical | | 2:2 |
| |
Scottish League Cup 1955, Group 5 |
| 20.08.1955 | | Hamilton Academical | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1954, Group 8 |
| 01.09.1954 | | Albion Rovers | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1954, Group 8 |
| 28.08.1954 | | Alloa Athletic | – | Arbroath | | 3:3 |
| |
Scottish League Cup 1954, Group 8 |
| 18.08.1954 | | Alloa Athletic | – | Albion Rovers | | 0:0 |
| |
Scottish League Cup 1952, Group 5 |
| 27.08.1952 | | Arbroath | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1952, Group 5 |
| 16.08.1952 | | Alloa Athletic | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1951, Group 6 |
| 25.08.1951 | | Alloa Athletic | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1950, Quarterfinal |
| 20.09.1950 | | Alloa Athletic | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1950, Group 8 |
| 02.09.1950 | | Alloa Athletic | – | Albion Rovers | | 2:2 |
| |
Scottish League Cup 1950, Group 8 |
| 16.08.1950 | | Arbroath | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1949, Group 7 |
| 17.08.1949 | | Alloa Athletic | – | Ayr United | | 2:2 |
| |
Scottish League Cup 1948, Quarterfinal |
| 30.10.1948 | | Dundee | – | Alloa Athletic | | 1:1 aet |
| |
Scottish League Cup 1947, Group 5 |
| 13.09.1947 | | Alloa Athletic | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1946/47, Section 5 |
| 21.09.1946 | | Alloa Athletic | – | St. Johnstone | | 0:0 |
| |
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