Scottish League Cup 2023/24, Group G |
 | 25.07.2023 |  | Queen of the South | – | East Fife | | 0:0,
pen. 3:5 |
| Dumfries |
Scottish League Cup 2023/24, Group G |
| 18.07.2023 | | Queen of the South | – | Motherwell | | 3:3 (1:1),
pen. 4:5 |
| Dumfries |
Scottish League Cup 2022/23, Group F |
| 16.07.2022 | | Queen of the South | – | St. Johnstone | | 2:2 (1:0),
pen. 4:2 |
| Dumfries |
Scottish League Cup 2020/21, Group G |
| 13.10.2020 | | Queen of the South | – | Partick Thistle | | 0:0,
pen. 2:3 |
| Dumfries |
Scottish League Cup 2020/21, Group G |
| 10.10.2020 | | Queen of the South | – | St. Mirren | | 2:2 (2:0),
pen. 2:4 |
| Dumfries |
Scottish League Cup 2020/21, Group G |
| 06.10.2020 | | Greenock Morton | – | Queen of the South | | 2:2 (1:0),
pen. 2:4 |
| Greenock |
Scottish League Cup 2019/20, Group E |
| 27.07.2019 | | Greenock Morton | – | Queen of the South | | 3:3 (2:1),
pen. 4:3 |
| Greenock |
Scottish League Cup 2019/20, Group E |
| 16.07.2019 | | Queen of the South | – | Annan Athletic | | 3:3 (3:1),
pen. 5:4 |
| Dumfries |
Scottish League Cup 2017/18, Group G |
| 29.07.2017 | | Queen of the South | – | Albion Rovers | | 2:2 (0:1),
pen. 4:3 |
| Dumfries |
Scottish League Cup 2017/18, Group G |
| 22.07.2017 | | Hamilton Academical | – | Queen of the South | | 1:1 (0:0),
pen. 6:5 |
| Hamilton |
Scottish League Cup 2017/18, Group G |
| 18.07.2017 | | Queen of the South | – | East Kilbride | | 0:0,
pen. 1:4 |
| Dumfries |
Scottish League Cup 2013/14, Third Round |
| 25.09.2013 | | Hearts | – | Queen of the South | | 3:3 aet
(1:1, 2:2),
pen. 4:2 |
| Edinburgh |
Scottish League Cup 1990, Second Round |
| 21.08.1990 | | Queen of the South | – | Dundee | | 2:2 aet,
pen. 4:1 |
| |
Scottish League Cup 1981, Group 5 |
| 26.08.1981 | | Queen of the South | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1977/78, Quarterfinal |
| 08.11.1977 | | Queen of the South | – | Forfar Athletic | | 3:3 |
| |
Scottish League Cup 1977/78, Third Round |
| 05.10.1977 | | Dundee | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Brechin City | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1977/78, First Round |
| 24.08.1977 | | Queen of the South | – | Hibernian | | 0:0 |
| |
Scottish League Cup 1976, Group 8 |
| 01.09.1976 | | Dunfermline Athletic | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1976, Group 8 |
| 21.08.1976 | | Queen of the South | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1975, Quarterfinal |
| 24.09.1975 | | Queen of the South | – | Rangers | | 2:2 aet |
| |
Scottish League Cup 1975, Group 5 |
| 16.08.1975 | | Falkirk | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1974, Group 5 |
| 17.08.1974 | | Berwick Rangers | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1974, Group 5 |
| 10.08.1974 | | Raith Rovers | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1973, Group 6 |
| 18.08.1973 | | Raith Rovers | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1970, Group 5 |
| 26.08.1970 | | Queen of the South | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1970, Group 5 |
| 19.08.1970 | | Queen of the South | – | Partick Thistle | | 0:0 |
| |
Scottish League Cup 1970, Group 5 |
| 15.08.1970 | | Stirling Albion | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1970, Group 5 |
| 08.08.1970 | | Queen of the South | – | East Fife | | 1:1 |
| |
Scottish League Cup 1968/69, Group 6 |
| 31.08.1968 | | Clydebank | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1968/69, Group 6 |
| 28.08.1968 | | East Fife | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1968/69, Group 6 |
| 14.08.1968 | | Queen of the South | – | East Fife | | 1:1 |
| |
Scottish League Cup 1968/69, Group 6 |
| 10.08.1968 | | Berwick Rangers | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1966, Group 7 |
| 31.08.1966 | | Airdrieonians | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1966, Group 7 |
| 20.08.1966 | | Dumbarton | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1965, Group 7 |
| 01.09.1965 | | Stranraer | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1965, Group 7 |
| 14.08.1965 | | Albion Rovers | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1964, Group 5 |
| 26.08.1964 | | Queen of the South | – | East Fife | | 1:1 |
| |
Scottish League Cup 1964, Group 5 |
| 15.08.1964 | | Queen of the South | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1963, Group 4 |
| 17.08.1963 | | Celtic | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1962, Group 7 |
| 01.09.1962 | | Montrose | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1962, Group 7 |
| 29.08.1962 | | Queen of the South | – | Queen's Park | | 4:4 |
| |
Scottish League Cup 1959, Group 7 |
| 22.08.1959 | | Forfar Athletic | – | Queen of the South | | 4:4 |
| |
Scottish League Cup 1959, Group 7 |
| 15.08.1959 | | Queen of the South | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1959, Group 7 |
| 08.08.1959 | | Queen of the South | – | Forfar Athletic | | 1:1 |
| |
Scottish League Cup 1957, Group 1 |
| 31.08.1957 | | Queen of the South | – | Falkirk | | 1:1 |
| |
Scottish League Cup 1956, Group 3 |
| 29.08.1956 | | Queen of the South | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1956, Group 3 |
| 25.08.1956 | | St. Mirren | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1956, Group 3 |
| 11.08.1956 | | Queen of the South | – | St. Mirren | | 0:0 |
| |
Scottish League Cup 1952, Group 2 |
| 16.08.1952 | | Queen of the South | – | Falkirk | | 2:2 |
| |
Scottish League Cup 1950, Quarterfinal |
| 20.09.1950 | | Alloa Athletic | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1950, Group 7 |
| 30.08.1950 | | Queen of the South | – | Stirling Albion | | 2:2 |
| |
Scottish League Cup 1950, Group 7 |
| 26.08.1950 | | Hamilton Academical | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1950, Group 7 |
| 19.08.1950 | | Queen's Park | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1949, Group 2 |
| 31.08.1949 | | Queen of the South | – | Falkirk | | 0:0 |
| |
Scottish League Cup 1949, Group 2 |
| 27.08.1949 | | Third Lanark | – | Queen of the South | | 1:1 |
| |
