Scottish League Cup 2023/24, Group E |
 | 22.07.2023 |  | Dumbarton | – | Bonnyrigg Rose Athletic | | 0:0,
pen. 4:3 |
| Dumbarton |
Scottish League Cup 2022/23, Group A |
| 19.07.2022 | | Dumbarton | – | Raith Rovers | | 0:0,
pen. 2:3 |
| Dumbarton |
Scottish League Cup 2018/19, Group H |
| 14.07.2018 | | Spartans | – | Dumbarton | | 0:0,
pen. 3:4 |
| Edinburgh |
Scottish League Cup 2017/18, Group E |
| 25.07.2017 | | Dumbarton | – | Annan Athletic | | 0:0,
pen. 3:4 |
| Dumbarton |
Scottish League Cup 2016/17, First Round, Group A |
| 30.07.2016 | | Dumbarton | – | Peterhead | | 3:3 (2:1),
pen. 5:6 |
| Dumbarton |
Scottish League Cup 2016/17, First Round, Group A |
| 16.07.2016 | | Forfar Athletic | – | Dumbarton | | 2:2 (1:0),
pen. 5:3 |
| Forfar |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | East Fife | – | Dumbarton | | 1:1 aet
(0:0, 1:1),
pen. 4:3 |
| Methil |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Dumbarton | – | Annan Athletic | | 1:1 aet
(0:0),
pen. 5:4 |
| Dumbarton |
Scottish League Cup 2000/01, First Round |
| 09.08.2000 | | Dumbarton | – | Ayr United | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 1997, First Round |
| 02.08.1997 | | Dumbarton | – | Queen's Park | | 1:1 aet,
pen. 6:5 |
| |
Scottish League Cup 1990, First Round |
| 14.08.1990 | | East Stirlingshire | – | Dumbarton | | 2:2 aet,
pen. 4:1 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Stirling Albion | – | Dumbarton | | 1:1 aet,
pen. 4:2 |
| |
Scottish League Cup 1980, Second Round |
| 30.08.1980 | | Raith Rovers | – | Dumbarton | | 1:1 aet |
| |
Scottish League Cup 1979, First Round |
| 15.08.1979 | | Dumbarton | – | St. Johnstone | | 1:1 |
| |
Scottish League Cup 1978/79, First Round |
| 16.08.1978 | | Dumbarton | – | St. Mirren | | 0:0 |
| |
Scottish League Cup 1976, Group 3 |
| 28.08.1976 | | Dundee United | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1976, Group 3 |
| 25.08.1976 | | Dumbarton | – | Celtic | | 3:3 |
| |
Scottish League Cup 1974, Group 1 |
| 28.08.1974 | | Clyde | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1974, Group 1 |
| 14.08.1974 | | Arbroath | – | Dumbarton | | 3:3 |
| |
Scottish League Cup 1973, Group 2 |
| 15.08.1973 | | Dumbarton | – | Morton | | 1:1 |
| |
Scottish League Cup 1972, Group 6 |
| 26.08.1972 | | Hearts | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1972, Group 6 |
| 23.08.1972 | | Dumbarton | – | Berwick Rangers | | 2:2 |
| |
Scottish League Cup 1971, Group 6 |
| 14.08.1971 | | Dumbarton | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1970, Semifinal |
| 07.10.1970 | | Dumbarton | – | Celtic | | 0:0 aet |
| |
Scottish League Cup 1970, Quarterfinal |
| 09.09.1970 | | Partick Thistle | – | Dumbarton | | 3:3 |
| |
Scottish League Cup 1970, Group 6 |
| 12.08.1970 | | Dumbarton | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1969, Supplementary Round |
| 01.09.1969 | | Brechin City | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1969, Group 7 |
| 16.08.1969 | | Stranraer | – | Dumbarton | | 2:2 |
| |
Scottish League Cup 1967, Group 7 |
| 26.08.1967 | | Dumbarton | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1966, Group 7 |
| 20.08.1966 | | Dumbarton | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1964, Group 8 |
| 26.08.1964 | | Berwick Rangers | – | Dumbarton | | 0:0 |
| |
Scottish League Cup 1964, Group 8 |
| 22.08.1964 | | Dumbarton | – | Morton | | 1:1 |
| |
Scottish League Cup 1964, Group 8 |
| 08.08.1964 | | Morton | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1963, Group 8 |
| 10.08.1963 | | Arbroath | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1962, Quarterfinal |
| 19.09.1962 | | Rangers | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1962, Supplementary Round |
| 03.09.1962 | | Dumbarton | – | Berwick Rangers | | 0:0 |
| |
Scottish League Cup 1962, Group 9 |
| 15.08.1962 | | Dumbarton | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1960, Group 7 |
| 03.09.1960 | | Dumbarton | – | Morton | | 3:3 |
| |
Scottish League Cup 1960, Group 7 |
| 17.08.1960 | | Dumbarton | – | Alloa Athletic | | 0:0 |
| |
Scottish League Cup 1960, Group 7 |
| 13.08.1960 | | Berwick Rangers | – | Dumbarton | | 2:2 |
| |
Scottish League Cup 1959, Group 6 |
| 12.08.1959 | | Dumbarton | – | Albion Rovers | | 3:3 |
| |
Scottish League Cup 1958, Group 7 |
| 09.08.1958 | | Dumbarton | – | Queen's Park | | 3:3 |
| |
Scottish League Cup 1956, Group 5 |
| 18.08.1956 | | Dumbarton | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1955, Quarterfinal |
| 17.09.1955 | | Dumbarton | – | St. Mirren | | 1:1 |
| |
Scottish League Cup 1955, Group 9 |
| 27.08.1955 | | Stranraer | – | Dumbarton | | 3:3 |
| |
Scottish League Cup 1953, Group 8 |
| 22.08.1953 | | Dumbarton | – | Forfar Athletic | | 0:0 |
| |
Scottish League Cup 1952, Group 6 |
| 27.08.1952 | | Dumbarton | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1951, Group 8 |
| 25.08.1951 | | Forfar Athletic | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1950, Group 5 |
| 02.09.1950 | | Kilmarnock | – | Dumbarton | | 0:0 |
| |
Scottish League Cup 1950, Group 5 |
| 30.08.1950 | | Dumbarton | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1949, Group 6 |
| 20.08.1949 | | Airdrieonians | – | Dumbarton | | 2:2 |
| |
Scottish League Cup 1948, Group 8 |
| 16.10.1948 | | Dumbarton | – | Arbroath | | 1:1 |
| |
Scottish League Cup 1947, Group 7 |
| 09.08.1947 | | Dumbarton | – | Stenhousemuir | | 5:5 |
| |
