Scottish League Cup 2020/21, Group F |
 | 14.11.2020 |  | Ayr United | – | Stranraer | | 1:1 (0:1),
pen. 6:5 |
| Ayr |
Scottish League Cup 2020/21, Group F |
| 13.10.2020 | | Stranraer | – | Albion Rovers | | 2:2 (1:2),
pen. 14:15 |
| Stranraer |
Scottish League Cup 2020/21, Group F |
| 10.10.2020 | | Annan Athletic | – | Stranraer | | 1:1 (0:1),
pen. 4:5 |
| Annan |
Scottish League Cup 2019/20, Group G |
| 27.07.2019 | | Ayr United | – | Stranraer | | 2:2 (2:1),
pen. 5:6 |
| Ayr |
Scottish League Cup 2018/19, Group G |
| 21.07.2018 | | Stranraer | – | Motherwell | | 1:1 (0:1),
pen. 3:2 |
| Stranraer |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Stranraer | – | Albion Rovers | | 1:1 aet,
pen. 4:3 |
| |
Scottish League Cup 1994, First Round |
| 10.08.1994 | | Stranraer | – | Cowdenbeath | | 2:2 aet,
pen. 4:2 |
| |
Scottish League Cup 1992, First Round |
| 01.08.1992 | | Stranraer | – | East Fife | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 1991, First Round |
| 13.08.1991 | | Alloa Athletic | – | Stranraer | | 0:0 aet,
pen. 8:7 |
| |
Scottish League Cup 1983/84, First Round |
| 17.08.1983 | | Stranraer | – | Berwick Rangers | | 1:1 |
| |
Scottish League Cup 1982, Group 9 |
| 14.08.1982 | | Albion Rovers | – | Stranraer | | 2:2 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | Stranraer | – | St. Johnstone | | 3:3 |
| |
Scottish League Cup 1979, First Round |
| 15.08.1979 | | Stranraer | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Clydebank | – | Stranraer | | 0:0 |
| |
Scottish League Cup 1976, Group 6 |
| 28.08.1976 | | Stranraer | – | Hamilton Academical | | 3:3 |
| |
Scottish League Cup 1975, Group 8 |
| 09.08.1975 | | Stranraer | – | Stenhousemuir | | 0:0 |
| |
Scottish League Cup 1974, Group 6 |
| 28.08.1974 | | Stranraer | – | Queen's Park | | 0:0 |
| |
Scottish League Cup 1974, Group 6 |
| 10.08.1974 | | Queen's Park | – | Stranraer | | 0:0 |
| |
Scottish League Cup 1971, Group 8 |
| 21.08.1971 | | Montrose | – | Stranraer | | 2:2 |
| |
Scottish League Cup 1970, Supplementary Round |
| 02.09.1970 | | Stranraer | – | Partick Thistle | | 2:2 |
| |
Scottish League Cup 1969, Group 7 |
| 23.08.1969 | | Stranraer | – | Cowdenbeath | | 3:3 |
| |
Scottish League Cup 1969, Group 7 |
| 16.08.1969 | | Stranraer | – | Dumbarton | | 2:2 |
| |
Scottish League Cup 1969, Group 7 |
| 13.08.1969 | | Stranraer | – | Clydebank | | 1:1 |
| |
Scottish League Cup 1969, Group 7 |
| 09.08.1969 | | Cowdenbeath | – | Stranraer | | 2:2 |
| |
Scottish League Cup 1968/69, Supplementary Round |
| 02.09.1968 | | Stranraer | – | Albion Rovers | | 3:3 |
| |
Scottish League Cup 1966, Group 9 |
| 20.08.1966 | | East Stirlingshire | – | Stranraer | | 0:0 |
| |
Scottish League Cup 1966, Group 9 |
| 17.08.1966 | | Stenhousemuir | – | Stranraer | | 1:1 |
| |
Scottish League Cup 1965, Group 7 |
| 01.09.1965 | | Stranraer | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1965, Group 7 |
| 21.08.1965 | | Stranraer | – | Albion Rovers | | 0:0 |
| |
Scottish League Cup 1964, Group 6 |
| 26.08.1964 | | East Stirlingshire Clydebank | – | Stranraer | | 3:3 |
| |
Scottish League Cup 1964, Group 6 |
| 15.08.1964 | | Stenhousemuir | – | Stranraer | | 3:3 |
| |
Scottish League Cup 1964, Group 6 |
| 12.08.1964 | | Stranraer | – | East Stirlingshire Clydebank | | 2:2 |
| |
Scottish League Cup 1964, Group 6 |
| 08.08.1964 | | Hamilton Academical | – | Stranraer | | 2:2 |
| |
Scottish League Cup 1961, Group 5 |
| 16.08.1961 | | Stranraer | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1960, Group 9 |
| 20.08.1960 | | Stranraer | – | East Fife | | 2:2 |
| |
Scottish League Cup 1956, Group 6 |
| 29.08.1956 | | Morton | – | Stranraer | | 1:1 |
| |
Scottish League Cup 1956, Group 6 |
| 11.08.1956 | | Cowdenbeath | – | Stranraer | | 1:1 |
| |
Scottish League Cup 1955, Group 9 |
| 27.08.1955 | | Stranraer | – | Dumbarton | | 3:3 |
| |
