Scottish League Cup 2023/24, Group D |
 | 22.07.2023 | | Stranraer | – | Edinburgh | | 2:1 (1:0) |
| Stranraer |
Scottish League Cup 2021/22, Group G |
| 17.07.2021 | | Stranraer | – | East Kilbride | | 1:0 (1:0) |
| Stranraer |
Scottish League Cup 2021/22, Group G |
| 10.07.2021 | | Stranraer | – | Greenock Morton | | 3:0 |
| Stranraer |
Scottish League Cup 2020/21, Group F |
| 11.11.2020 | | Stranraer | – | Hamilton Academical | | 2:1 (1:0) |
| Stranraer |
Scottish League Cup 2019/20, Group G |
| 20.07.2019 | | Stranraer | – | Berwick Rangers | | 6:0 (4:0) |
| Stranraer |
Scottish League Cup 2016/17, First Round, Group F |
| 19.07.2016 | | Stranraer | – | East Stirlingshire | | 3:1 (0:0) |
| Stranraer |
Scottish League Cup 2016/17, First Round, Group F |
| 16.07.2016 | | Annan Athletic | – | Stranraer | | 1:2 (0:0) |
| Annan |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | Stranraer | – | Stenhousemuir | | 2:0 (1:0) |
| Stranraer |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Stranraer | – | East Fife | | 1:0 (0:0) |
| Stranraer |
Scottish League Cup 2013/14, Second Round |
| 27.08.2013 | | Stranraer | – | Ross County | | 3:2 (0:1) |
| Stranraer |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Stranraer | – | Brechin City | | 4:3 (3:0) |
| Stranraer |
Scottish League Cup 2005/06, Second Round |
| 23.08.2005 | | Stranraer | – | Dundee | | 3:1 (2:0) |
| |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | East Fife | – | Stranraer | | 0:1 (0:0) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Stranraer | – | Raith Rovers | | 2:1 (0:0) |
| |
Scottish League Cup 2002/03, First Round |
| 07.09.2002 | | Stranraer | – | Brechin City | | 6:1 (5:0) |
| |
Scottish League Cup 2001/02, First Round |
| 02.09.2001 | | Elgin City | – | Stranraer | | 2:3 |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | Stranraer | – | Queen of the South | | 2:0 |
| |
Scottish League Cup 1993, First Round |
| 04.08.1993 | | Queen of the South | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1992, Second Round |
| 11.08.1992 | | Airdrieonians | – | Stranraer | | 2:3 |
| |
Scottish League Cup 1990, Second Round |
| 21.08.1990 | | Airdrieonians | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1990, First Round |
| 15.08.1990 | | Stranraer | – | Berwick Rangers | | 4:3 |
| |
Scottish League Cup 1988, First Round |
| 10.08.1988 | | Queen's Park | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1985, First Round |
| 14.08.1985 | | Stranraer | – | Albion Rovers | | 3:0 |
| |
Scottish League Cup 1982, Group 9 |
| 25.08.1982 | | Stenhousemuir | – | Stranraer | | 0:4 |
| |
Scottish League Cup 1981, Group 9 |
| 19.08.1981 | | Stranraer | – | Albion Rovers | | 2:0 |
| |
Scottish League Cup 1981, Group 9 |
| 12.08.1981 | | Stenhousemuir | – | Stranraer | | 2:3 |
| |
Scottish League Cup 1979, First Round |
| 22.08.1979 | | Dunfermline Athletic | – | Stranraer | | 2:4 aet |
| |
Scottish League Cup 1977/78, First Round |
| 24.08.1977 | | Stranraer | – | Alloa Athletic | | 3:0 |
| |
Scottish League Cup 1976, Group 6 |
| 01.09.1976 | | Stranraer | – | East Fife | | 5:0 |
| |
Scottish League Cup 1976, Group 6 |
| 18.08.1976 | | Stranraer | – | Falkirk | | 5:0 |
| |
Scottish League Cup 1975, Group 8 |
| 20.08.1975 | | Stranraer | – | Morton | | 2:1 |
| |
Scottish League Cup 1975, Group 8 |
| 16.08.1975 | | Stranraer | – | Albion Rovers | | 3:2 |
| |
Scottish League Cup 1975, Group 8 |
| 13.08.1975 | | Morton | – | Stranraer | | 2:5 |
| |
Scottish League Cup 1973, Group 9 |
| 22.08.1973 | | Stranraer | – | Albion Rovers | | 4:0 |
| |
Scottish League Cup 1973, Group 9 |
| 11.08.1973 | | Stranraer | – | Brechin City | | 2:1 |
| |
Scottish League Cup 1972, Group 1 |
| 23.08.1972 | | Cowdenbeath | – | Stranraer | | 0:2 |
| |
Scottish League Cup 1972, Group 1 |
| 16.08.1972 | | Stranraer | – | Cowdenbeath | | 3:0 |
| |
Scottish League Cup 1972, Group 1 |
| 12.08.1972 | | Morton | – | Stranraer | | 1:5 |
| |
Scottish League Cup 1971, Group 8 |
| 28.08.1971 | | Stranraer | – | Albion Rovers | | 2:0 |
| |
Scottish League Cup 1971, Group 8 |
| 18.08.1971 | | Stranraer | – | St. Mirren | | 2:0 |
| |
Scottish League Cup 1970, Group 9 |
| 22.08.1970 | | Stranraer | – | Forfar Athletic | | 1:0 |
| |
Scottish League Cup 1970, Group 9 |
| 19.08.1970 | | Stranraer | – | Stenhousemuir | | 4:0 |
| |
Scottish League Cup 1970, Group 9 |
| 08.08.1970 | | Hamilton Academical | – | Stranraer | | 2:3 |
| |
Scottish League Cup 1968/69, Supplementary Round |
| 04.09.1968 | | Albion Rovers | – | Stranraer | | 0:2 |
| |
Scottish League Cup 1968/69, Group 9 |
| 31.08.1968 | | Alloa Athletic | – | Stranraer | | 0:1 |
| |
Scottish League Cup 1968/69, Group 9 |
| 14.08.1968 | | Stenhousemuir | – | Stranraer | | 1:3 |
| |
Scottish League Cup 1968/69, Group 9 |
| 10.08.1968 | | Stranraer | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1967, Group 5 |
| 30.08.1967 | | Stranraer | – | Berwick Rangers | | 1:0 |
| |
Scottish League Cup 1966, Group 9 |
| 27.08.1966 | | Stranraer | – | Clydebank | | 1:0 |
| |
Scottish League Cup 1966, Group 9 |
| 13.08.1966 | | Stranraer | – | Forfar Athletic | | 2:1 |
| |
Scottish League Cup 1965, Group 7 |
| 18.08.1965 | | Queen of the South | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1964, Group 6 |
| 29.08.1964 | | Stranraer | – | Stenhousemuir | | 1:0 |
| |
Scottish League Cup 1964, Group 6 |
| 22.08.1964 | | Stranraer | – | Hamilton Academical | | 2:1 |
| |
Scottish League Cup 1963, Group 6 |
| 31.08.1963 | | Ayr United | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1963, Group 6 |
| 17.08.1963 | | Stranraer | – | Ayr United | | 2:1 |
| |
Scottish League Cup 1962, Group 6 |
| 15.08.1962 | | Stranraer | – | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1961, Group 5 |
| 02.09.1961 | | Stranraer | – | Stirling Albion | | 3:0 |
| |
Scottish League Cup 1960, Group 9 |
| 03.09.1960 | | Stranraer | – | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1960, Group 9 |
| 17.08.1960 | | East Stirlingshire | – | Stranraer | | 1:3 |
| |
Scottish League Cup 1959, Group 9 |
| 29.08.1959 | | Stranraer | – | Montrose | | 4:2 |
| |
Scottish League Cup 1959, Group 9 |
| 22.08.1959 | | Stranraer | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1958, Group 9 |
| 27.08.1958 | | Stenhousemuir | – | Stranraer | | 3:4 |
| |
Scottish League Cup 1958, Group 9 |
| 23.08.1958 | | Stranraer | – | Berwick Rangers | | 2:1 |
| |
Scottish League Cup 1958, Group 9 |
| 16.08.1958 | | East Stirlingshire | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1958, Group 9 |
| 09.08.1958 | | Stranraer | – | Albion Rovers | | 4:1 |
| |
Scottish League Cup 1957, Group 5 |
| 10.08.1957 | | Stranraer | – | Dumbarton | | 3:1 |
| |
Scottish League Cup 1956, Group 6 |
| 18.08.1956 | | Stranraer | – | Berwick Rangers | | 5:2 |
| |
Scottish League Cup 1955, Group 9 |
| 13.08.1955 | | Stranraer | – | Montrose | | 3:2 |
| |
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