Scottish League Cup 2023/24, Group E |
 | 18.07.2023 | | Dumbarton | – | Inverness | | 2:1 (1:0) |
| Dumbarton |
Scottish League Cup 2022/23, Group A |
| 16.07.2022 | | Peterhead | – | Dumbarton | | 0:2 (0:1) |
| Peterhead |
Scottish League Cup 2019/20, Group E |
| 13.07.2019 | | Annan Athletic | – | Dumbarton | | 0:1 (0:0) |
| Annan |
Scottish League Cup 2018/19, Group H |
| 17.07.2018 | | Dumbarton | – | Queen's Park | | 1:0 (1:0) |
| Dumbarton |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Brechin City | – | Dumbarton | | 0:1 (0:0) |
| Brechin |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Dumbarton | – | Albion Rovers | | 1:0 (1:0) |
| Dumbarton |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Dumbarton | – | Albion Rovers | | 2:0 (1:0) |
| Dumbarton |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Dumbarton | – | Stirling Albion | | 3:0 (0:0) |
| Dumbarton |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | Ayr United | – | Dumbarton | | 1:2 (0:1) |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | Dumbarton | – | Clydebank | | 2:0 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Brechin City | – | Dumbarton | | 0:2 |
| |
Scottish League Cup 1991, First Round |
| 14.08.1991 | | Berwick Rangers | – | Dumbarton | | 0:1 |
| |
Scottish League Cup 1989, First Round |
| 08.08.1989 | | Dumbarton | – | Stenhousemuir | | 3:0 |
| |
Scottish League Cup 1987, Second Round |
| 19.08.1987 | | Ayr United | – | Dumbarton | | 0:1 |
| |
Scottish League Cup 1986, Second Round |
| 20.08.1986 | | Dumbarton | – | Stirling Albion | | 1:0 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Queen of the South | – | Dumbarton | | 1:2 |
| |
Scottish League Cup 1981, Group 5 |
| 22.08.1981 | | Dumbarton | – | Cowdenbeath | | 3:0 |
| |
Scottish League Cup 1981, Group 5 |
| 12.08.1981 | | Dumbarton | – | Queen of the South | | 1:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Dumbarton | – | Hamilton Academical | | 4:1 |
| |
Scottish League Cup 1976, Group 3 |
| 01.09.1976 | | Arbroath | – | Dumbarton | | 0:3 |
| |
Scottish League Cup 1976, Group 3 |
| 14.08.1976 | | Dumbarton | – | Arbroath | | 2:0 |
| |
Scottish League Cup 1975, Group 3 |
| 09.08.1975 | | Dumbarton | – | Hearts | | 2:1 |
| |
Scottish League Cup 1974, Group 1 |
| 24.08.1974 | | Dumbarton | – | Partick Thistle | | 3:1 |
| |
Scottish League Cup 1974, Group 1 |
| 17.08.1974 | | Partick Thistle | – | Dumbarton | | 1:2 |
| |
Scottish League Cup 1973, Group 2 |
| 29.08.1973 | | Dumbarton | – | Ayr United | | 1:0 |
| |
Scottish League Cup 1973, Group 2 |
| 25.08.1973 | | Dumbarton | – | Hibernian | | 4:1 |
| |
Scottish League Cup 1972, Second Round |
| 20.09.1972 | | Dumbarton | – | Dundee | | 3:0 |
| |
Scottish League Cup 1972, Group 6 |
| 19.08.1972 | | Dumbarton | – | Airdrieonians | | 4:1 |
| |
Scottish League Cup 1972, Group 6 |
| 12.08.1972 | | Dumbarton | – | Hearts | | 1:0 |
| |
Scottish League Cup 1971, Group 6 |
| 18.08.1971 | | Stenhousemuir | – | Dumbarton | | 2:3 |
| |
Scottish League Cup 1970, Quarterfinal |
| 23.09.1970 | | Dumbarton | – | Partick Thistle | | 3:2 |
| |
Scottish League Cup 1970, Group 6 |
| 26.08.1970 | | Dumbarton | – | Berwick Rangers | | 3:2 |
| |
Scottish League Cup 1970, Group 6 |
| 22.08.1970 | | Dumbarton | – | Alloa Athletic | | 5:2 |
| |
Scottish League Cup 1970, Group 6 |
| 19.08.1970 | | Brechin City | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1970, Group 6 |
| 15.08.1970 | | Berwick Rangers | – | Dumbarton | | 0:2 |
| |
Scottish League Cup 1970, Group 6 |
| 08.08.1970 | | Alloa Athletic | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1969, Supplementary Round |
| 03.09.1969 | | Dumbarton | – | Brechin City | | 5:2 |
| |
Scottish League Cup 1969, Group 7 |
| 27.08.1969 | | Dumbarton | – | Stranraer | | 2:0 |
| |
Scottish League Cup 1969, Group 7 |
| 23.08.1969 | | Dumbarton | – | Clydebank | | 1:0 |
| |
Scottish League Cup 1969, Group 7 |
| 20.08.1969 | | Cowdenbeath | – | Dumbarton | | 2:3 |
| |
Scottish League Cup 1969, Group 7 |
| 09.08.1969 | | Clydebank | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1968/69, Group 8 |
| 28.08.1968 | | Dumbarton | – | Forfar Athletic | | 5:1 |
| |
Scottish League Cup 1968/69, Group 8 |
| 17.08.1968 | | Dumbarton | – | Queen's Park | | 4:3 |
| |
Scottish League Cup 1966, Group 7 |
| 31.08.1966 | | Queen's Park | – | Dumbarton | | 0:3 |
| |
Scottish League Cup 1965, Group 8 |
| 04.09.1965 | | Dumbarton | – | Alloa Athletic | | 4:1 |
| |
Scottish League Cup 1965, Group 8 |
| 01.09.1965 | | Dumbarton | – | East Fife | | 6:1 |
| |
Scottish League Cup 1965, Group 8 |
| 14.08.1965 | | Dumbarton | – | East Stirlingshire Clydebank | | 2:1 |
| |
Scottish League Cup 1964, Group 8 |
| 29.08.1964 | | Dumbarton | – | Ayr United | | 2:1 |
| |
Scottish League Cup 1964, Group 8 |
| 12.08.1964 | | Dumbarton | – | Berwick Rangers | | 3:2 |
| |
Scottish League Cup 1963, Group 8 |
| 28.08.1963 | | Raith Rovers | – | Dumbarton | | 1:2 |
| |
Scottish League Cup 1963, Group 8 |
| 14.08.1963 | | Dumbarton | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1962, Supplementary Round |
| 05.09.1962 | | Berwick Rangers | – | Dumbarton | | 1:2 |
| |
Scottish League Cup 1962, Group 9 |
| 25.08.1962 | | Dumbarton | – | Forfar Athletic | | 1:0 |
| |
Scottish League Cup 1962, Group 9 |
| 18.08.1962 | | Brechin City | – | Dumbarton | | 3:5 |
| |
Scottish League Cup 1962, Group 9 |
| 11.08.1962 | | Albion Rovers | – | Dumbarton | | 3:5 |
| |
Scottish League Cup 1961, Group 8 |
| 02.09.1961 | | Dumbarton | – | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1960, Quarterfinal |
| 21.09.1960 | | Dumbarton | – | Queen of the South | | 2:1 |
| |
Scottish League Cup 1960, Supplementary Round |
| 05.09.1960 | | Dumbarton | – | Cowdenbeath | | 3:0 |
| |
Scottish League Cup 1960, Group 7 |
| 31.08.1960 | | Alloa Athletic | – | Dumbarton | | 1:5 |
| |
Scottish League Cup 1960, Group 7 |
| 27.08.1960 | | Dumbarton | – | Berwick Rangers | | 3:0 |
| |
Scottish League Cup 1960, Group 7 |
| 20.08.1960 | | Morton | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1959, Group 6 |
| 15.08.1959 | | Stenhousemuir | – | Dumbarton | | 0:2 |
| |
Scottish League Cup 1958, Group 7 |
| 27.08.1958 | | Dumbarton | – | Alloa Athletic | | 3:1 |
| |
Scottish League Cup 1958, Group 7 |
| 23.08.1958 | | Queen's Park | – | Dumbarton | | 0:3 |
| |
Scottish League Cup 1958, Group 7 |
| 13.08.1958 | | Alloa Athletic | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1957, Group 5 |
| 28.08.1957 | | Dundee United | – | Dumbarton | | 0:3 |
| |
Scottish League Cup 1957, Group 5 |
| 24.08.1957 | | Dumbarton | – | Stranraer | | 10:3 |
| |
Scottish League Cup 1956, Group 5 |
| 01.09.1956 | | Alloa Athletic | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1956, Group 5 |
| 25.08.1956 | | Brechin City | – | Dumbarton | | 3:4 |
| |
Scottish League Cup 1955, Supplementary Round |
| 08.09.1955 | | Morton | – | Dumbarton | | 0:1 |
| |
Scottish League Cup 1955, Supplementary Round |
| 06.09.1955 | | Dumbarton | – | Morton | | 2:1 |
| |
Scottish League Cup 1955, Group 9 |
| 03.09.1955 | | Dumbarton | – | East Stirlingshire | | 6:1 |
| |
Scottish League Cup 1955, Group 9 |
| 20.08.1955 | | Montrose | – | Dumbarton | | 0:2 |
| |
Scottish League Cup 1955, Group 9 |
| 13.08.1955 | | Dumbarton | – | Berwick Rangers | | 2:0 |
| |
Scottish League Cup 1953, Group 8 |
| 15.08.1953 | | Dumbarton | – | Arbroath | | 3:0 |
| |
Scottish League Cup 1952, Group 6 |
| 30.08.1952 | | Dumbarton | – | Stirling Albion | | 2:1 |
| |
Scottish League Cup 1952, Group 6 |
| 09.08.1952 | | Dumbarton | – | Dundee United | | 3:1 |
| |
Scottish League Cup 1951, Group 8 |
| 18.08.1951 | | Dumbarton | – | Kilmarnock | | 1:0 |
| |
Scottish League Cup 1950, Group 5 |
| 19.08.1950 | | Dumbarton | – | Kilmarnock | | 1:0 |
| |
Scottish League Cup 1949, Group 6 |
| 31.08.1949 | | Dumbarton | – | Dundee United | | 3:1 |
| |
Scottish League Cup 1949, Group 6 |
| 13.08.1949 | | Dumbarton | – | Arbroath | | 5:1 |
| |
Scottish League Cup 1948, Group 8 |
| 02.10.1948 | | Dumbarton | – | Airdrieonians | | 5:0 |
| |
Scottish League Cup 1947, Group 7 |
| 06.09.1947 | | Dumbarton | – | Arbroath | | 4:2 |
| |
Scottish League Cup 1947, Group 7 |
| 16.08.1947 | | Arbroath | – | Dumbarton | | 1:3 |
| |
Scottish League Cup 1946/47, Section 7 |
| 26.10.1946 | | Cowdenbeath | – | Dumbarton | | 2:3 |
| |
Scottish League Cup 1946/47, Section 7 |
| 12.10.1946 | | Dumbarton | – | Arbroath | | 8:0 |
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