Scottish League Cup 2023/24, Group A |
| 25.07.2023 | | Stenhousemuir | | Alloa Athletic | | 1:3 (1:1) |
| Stenhousemuir |
Scottish League Cup 2022/23, Group C |
| 16.07.2022 | | Buckie Thistle | | Alloa Athletic | | 1:4 (1:2) |
| Buckie |
Scottish League Cup 2021/22, Group D |
| 17.07.2021 | | Alloa Athletic | | Livingston | | 2:1 (0:0) |
| Alloa |
Scottish League Cup 2020/21, Second round |
| 28.11.2020 | | Alloa Athletic | | Hearts | | 1:0 aet (0:0, 0:0) |
| Alloa |
Scottish League Cup 2020/21, Group H |
| 14.11.2020 | | Alloa Athletic | | Stenhousemuir | | 4:2 (0:2) |
| Alloa |
Scottish League Cup 2020/21, Group H |
| 13.10.2020 | | Alloa Athletic | | Edinburgh City | | 2:1 (1:0) |
| Alloa |
Scottish League Cup 2020/21, Group H |
| 07.10.2020 | | Airdrieonians | | Alloa Athletic | | 0:2 (0:1) |
| Airdrie |
Scottish League Cup 2019/20, Group C |
| 27.07.2019 | | Arbroath | | Alloa Athletic | | 2:3 (1:1) |
| Arbroath |
Scottish League Cup 2019/20, Group C |
| 23.07.2019 | | Alloa Athletic | | Stirling Albion | | 2:1 (0:0) |
| Alloa |
Scottish League Cup 2018/19, Group A |
| 24.07.2018 | | Elgin City | | Alloa Athletic | | 0:3 (0:2) |
| Elgin |
Scottish League Cup 2018/19, Group A |
| 17.07.2018 | | Alloa Athletic | | Arbroath | | 4:2 (4:2) |
| Alloa |
Scottish League Cup 2016/17, Second round |
| 09.08.2016 | | Alloa Athletic | | Inverness | | 1:0 (1:0) |
| Alloa |
Scottish League Cup 2016/17, First Round, Group D |
| 30.07.2016 | | Raith Rovers | | Alloa Athletic | | 0:1 (0:1) |
| Kirkcaldy |
Scottish League Cup 2016/17, First Round, Group D |
| 26.07.2016 | | Alloa Athletic | | Ross County | | 3:2 (2:2) |
| Alloa |
Scottish League Cup 2016/17, First Round, Group D |
| 23.07.2016 | | Montrose | | Alloa Athletic | | 0:2 (0:1) |
| Montrose |
Scottish League Cup 2016/17, First Round, Group D |
| 19.07.2016 | | Alloa Athletic | | Cove Rangers | | 4:0 (1:0) |
| Alloa |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Alloa Athletic | | Stirling Albion | | 1:0 (1:0) |
| Alloa |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Peterhead | | Alloa Athletic | | 0:2 (0:0) |
| Peterhead |
Scottish League Cup 2010/11, First Round |
| 01.08.2010 | | East Stirlingshire | | Alloa Athletic | | 1:2 (1:1) |
| Stenhousemuir |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Alloa Athletic | | Elgin City | | 2:0 (0:0) |
| Alloa |
Scottish League Cup 2006/07, Second Round |
| 22.08.2006 | | Alloa Athletic | | Ross County | | 2:1 (1:0) |
| Alloa |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Forfar Athletic | | Alloa Athletic | | 1:2 aet (0:1, 1:1) |
| Forfar |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | Alloa Athletic | | Arbroath | | 2:1 aet (1:1, 1:1) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | St. Johnstone | | Alloa Athletic | | 2:3 (0:1) |
| |
Scottish League Cup 2002/03, First Round |
| 10.09.2002 | | Raith Rovers | | Alloa Athletic | | 2:3 aet (0:1, 2:2) |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | Alloa Athletic | | Peterhead | | 4:0 |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | Clydebank | | Alloa Athletic | | 0:2 |
| |
Scottish League Cup 1999/00, Second Round |
| 17.08.1999 | | Greenock Morton | | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Partick Thistle | | Alloa Athletic | | 0:2 |
| |
Scottish League Cup 1998, Second Round |
| 08.08.1998 | | Dundee | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Dumbarton | | Alloa Athletic | | 0:4 |
| |
Scottish League Cup 1997, First Round |
| 02.08.1997 | | Cowdenbeath | | Alloa Athletic | | 0:2 |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | East Stirlingshire | | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1995, First Round |
| 05.08.1995 | | Alloa Athletic | | Forfar Athletic | | 2:1 |
| |
Scottish League Cup 1993, First Round |
| 03.08.1993 | | Alloa Athletic | | Berwick Rangers | | 1:0 |
| |
Scottish League Cup 1992, First Round |
| 01.08.1992 | | East Stirlingshire | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1983/84, Group 1 |
| 30.11.1983 | | Alloa Athletic | | Morton | | 1:0 |
| |
Scottish League Cup 1983/84, Group 1 |
| 05.10.1983 | | Morton | | Alloa Athletic | | 2:4 |
| |
Scottish League Cup 1983/84, Second Round |
| 24.08.1983 | | Falkirk | | Alloa Athletic | | 2:3 |
| |
Scottish League Cup 1982, Group 1 |
| 01.09.1982 | | Alloa Athletic | | Dunfermline Athletic | | 3:0 |
| |
Scottish League Cup 1982, Group 1 |
| 14.08.1982 | | Arbroath | | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1981, Group 6 |
| 15.08.1981 | | Alloa Athletic | | Stirling Albion | | 4:3 |
| |
Scottish League Cup 1978/79, First Round |
| 23.08.1978 | | Stirling Albion | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1978/79, First Round |
| 16.08.1978 | | Alloa Athletic | | Stirling Albion | | 4:1 |
| |
Scottish League Cup 1977/78, First Round |
| 17.08.1977 | | Alloa Athletic | | Stranraer | | 5:3 |
| |
Scottish League Cup 1976, Group 8 |
| 28.08.1976 | | Alloa Athletic | | Queen of the South | | 1:0 |
| |
Scottish League Cup 1976, Group 8 |
| 25.08.1976 | | Alloa Athletic | | Dunfermline Athletic | | 4:0 |
| |
Scottish League Cup 1976, Group 8 |
| 14.08.1976 | | Alloa Athletic | | Clydebank | | 1:0 |
| |
Scottish League Cup 1975, Group 9 |
| 18.08.1975 | | Meadowbank Thistle | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1974, Group 8 |
| 21.08.1974 | | Alloa Athletic | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1973, Group 7 |
| 15.08.1973 | | Alloa Athletic | | Montrose | | 3:1 |
| |
Scottish League Cup 1972, Supplementary Round |
| 06.09.1972 | | Ayr United | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1972, Group 9 |
| 26.08.1972 | | Alloa Athletic | | Hamilton Academical | | 2:0 |
| |
Scottish League Cup 1972, Group 9 |
| 23.08.1972 | | Brechin City | | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1972, Group 9 |
| 16.08.1972 | | Alloa Athletic | | Albion Rovers | | 4:3 |
| |
Scottish League Cup 1971, Group 9 |
| 14.08.1971 | | Alloa Athletic | | Hamilton Academical | | 3:0 |
| |
Scottish League Cup 1970, Group 6 |
| 26.08.1970 | | Alloa Athletic | | Brechin City | | 2:0 |
| |
Scottish League Cup 1970, Group 6 |
| 15.08.1970 | | Brechin City | | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1969, Group 9 |
| 23.08.1969 | | Berwick Rangers | | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1969, Group 9 |
| 20.08.1969 | | Alloa Athletic | | Brechin City | | 2:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 14.08.1968 | | Brechin City | | Alloa Athletic | | 2:3 |
| |
Scottish League Cup 1966, Group 8 |
| 31.08.1966 | | Alloa Athletic | | Montrose | | 1:0 |
| |
Scottish League Cup 1966, Group 8 |
| 20.08.1966 | | Alloa Athletic | | Hamilton Academical | | 3:1 |
| |
Scottish League Cup 1966, Group 8 |
| 13.08.1966 | | Alloa Athletic | | Albion Rovers | | 4:0 |
| |
Scottish League Cup 1965, Group 8 |
| 01.09.1965 | | Alloa Athletic | | East Stirlingshire Clydebank | | 2:1 |
| |
Scottish League Cup 1965, Group 8 |
| 28.08.1965 | | East Fife | | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1965, Group 8 |
| 21.08.1965 | | Alloa Athletic | | Dumbarton | | 2:1 |
| |
Scottish League Cup 1965, Group 8 |
| 14.08.1965 | | Alloa Athletic | | East Fife | | 3:2 |
| |
Scottish League Cup 1964, Group 9 |
| 29.08.1964 | | Alloa Athletic | | Stirling Albion | | 2:1 |
| |
Scottish League Cup 1964, Group 9 |
| 15.08.1964 | | Brechin City | | Alloa Athletic | | 3:5 |
| |
Scottish League Cup 1963, Group 5 |
| 31.08.1963 | | Albion Rovers | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1962, Group 8 |
| 25.08.1962 | | Alloa Athletic | | Stirling Albion | | 2:1 |
| |
Scottish League Cup 1961, Group 5 |
| 30.08.1961 | | Alloa Athletic | | Stranraer | | 2:0 |
| |
Scottish League Cup 1960, Group 7 |
| 03.09.1960 | | Alloa Athletic | | Berwick Rangers | | 2:1 |
| |
Scottish League Cup 1960, Group 7 |
| 20.08.1960 | | Berwick Rangers | | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1959, Group 8 |
| 22.08.1959 | | Morton | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1959, Group 8 |
| 08.08.1959 | | Alloa Athletic | | Morton | | 4:2 |
| |
Scottish League Cup 1957, Group 9 |
| 24.08.1957 | | Forfar Athletic | | Alloa Athletic | | 2:3 |
| |
Scottish League Cup 1957, Group 9 |
| 17.08.1957 | | Alloa Athletic | | Berwick Rangers | | 5:0 |
| |
Scottish League Cup 1956, Group 5 |
| 11.08.1956 | | Alloa Athletic | | Hamilton Academical | | 3:1 |
| |
Scottish League Cup 1955, Group 5 |
| 31.08.1955 | | Alloa Athletic | | Cowdenbeath | | 5:3 |
| |
Scottish League Cup 1955, Group 5 |
| 27.08.1955 | | Arbroath | | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1955, Group 5 |
| 13.08.1955 | | Alloa Athletic | | Arbroath | | 5:3 |
| |
Scottish League Cup 1954, Group 8 |
| 04.09.1954 | | Alloa Athletic | | Morton | | 1:0 |
| |
Scottish League Cup 1954, Group 8 |
| 14.08.1954 | | Arbroath | | Alloa Athletic | | 2:3 |
| |
Scottish League Cup 1953, Group 5 |
| 26.08.1953 | | Alloa Athletic | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1952, Group 5 |
| 13.08.1952 | | Alloa Athletic | | Arbroath | | 3:1 |
| |
Scottish League Cup 1951, Group 6 |
| 18.08.1951 | | Hamilton Academical | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1951, Group 6 |
| 15.08.1951 | | Alloa Athletic | | Queen's Park | | 2:0 |
| |
Scottish League Cup 1950, Group 8 |
| 30.08.1950 | | Alloa Athletic | | Arbroath | | 3:1 |
| |
Scottish League Cup 1950, Group 8 |
| 19.08.1950 | | Albion Rovers | | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1950, Group 8 |
| 12.08.1950 | | Alloa Athletic | | Forfar Athletic | | 6:0 |
| |
Scottish League Cup 1948, Group 6 |
| 16.10.1948 | | Alloa Athletic | | Kilmarnock | | 2:0 |
| |
Scottish League Cup 1948, Group 6 |
| 09.10.1948 | | East Stirlingshire | | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1948, Group 6 |
| 02.10.1948 | | Alloa Athletic | | Queen's Park | | 1:0 |
| |
Scottish League Cup 1948, Group 6 |
| 18.09.1948 | | Alloa Athletic | | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1946/47, Section 5 |
| 26.10.1946 | | Alloa Athletic | | Dunfermline Athletic | | 2:1 |
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