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 |
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