Scottish League Cup 2023/24, Group A |
 | 15.07.2023 |  | Stirling Albion | – | Ayr United | | 1:1 (1:0),
pen. 3:4 |
| Stirling |
Scottish League Cup 2022/23, Group A |
| 16.07.2022 | | Raith Rovers | – | Stirling Albion | | 1:1 (1:1),
pen. 4:5 |
| Kirkcaldy |
Scottish League Cup 2021/22, Group A |
| 17.07.2021 | | Inverness | – | Stirling Albion | | 2:2 (1:2),
pen. 2:3 |
| Inverness |
Scottish League Cup 2019/20, Group C |
| 13.07.2019 | | Stirling Albion | – | Hibernian | | 1:1 (0:1),
pen. 4:5 |
| Stirling |
Scottish League Cup 2017/18, Group A |
| 18.07.2017 | | Stirling Albion | – | Inverness | | 0:0,
pen. 0:2 |
| Stirling |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Arbroath | – | Stirling Albion | | 1:1 aet
(0:1, 1:1),
pen. 3:2 |
| Arbroath |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Stirling Albion | – | Ayr United | | 1:1 aet
(1:0, 1:1) |
| Stirling |
Scottish League Cup 2002/03, First Round |
| 11.09.2002 | | Stirling Albion | – | Stenhousemuir | | 3:3 aet,
pen. 4:2 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | East Fife | – | Stirling Albion | | 2:2 aet,
pen. 8:7 |
| |
Scottish League Cup 1998, Second Round |
| 08.08.1998 | | Dundee United | – | Stirling Albion | | 2:2 aet,
pen. 3:0 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Stirling Albion | – | Dumbarton | | 1:1 aet,
pen. 4:2 |
| |
Scottish League Cup 1983/84, First Round |
| 15.08.1983 | | Stirling Albion | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1982, Group 6 |
| 01.09.1982 | | St. Mirren | – | Stirling Albion | | 0:0 |
| |
Scottish League Cup 1982, Group 6 |
| 25.08.1982 | | Stirling Albion | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1982, Group 6 |
| 18.08.1982 | | Ayr United | – | Stirling Albion | | 0:0 |
| |
Scottish League Cup 1981, Group 6 |
| 26.08.1981 | | Stirling Albion | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1981, Group 6 |
| 22.08.1981 | | Stirling Albion | – | Falkirk | | 0:0 |
| |
Scottish League Cup 1977/78, Third Round |
| 26.10.1977 | | Celtic | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Stirling Albion | – | East Stirlingshire | | 0:0 |
| |
Scottish League Cup 1976, Group 7 |
| 21.08.1976 | | Stirling Albion | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1976, Group 7 |
| 18.08.1976 | | Stirling Albion | – | Cowdenbeath | | 0:0 |
| |
Scottish League Cup 1975, Group 5 |
| 16.08.1975 | | Hamilton Academical | – | Stirling Albion | | 0:0 |
| |
Scottish League Cup 1972, Group 8 |
| 19.08.1972 | | East Fife | – | Stirling Albion | | 0:0 |
| |
Scottish League Cup 1971, Group 6 |
| 14.08.1971 | | Dumbarton | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1970, Group 5 |
| 26.08.1970 | | Queen of the South | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1970, Group 5 |
| 22.08.1970 | | Partick Thistle | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1970, Group 5 |
| 15.08.1970 | | Stirling Albion | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1970, Group 5 |
| 12.08.1970 | | East Fife | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1967, Group 4 |
| 26.08.1967 | | Stirling Albion | – | Falkirk | | 1:1 |
| |
Scottish League Cup 1966, Group 2 |
| 31.08.1966 | | Rangers | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1966, Group 2 |
| 27.08.1966 | | Stirling Albion | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1963, Quarterfinal |
| 11.09.1963 | | Stirling Albion | – | Berwick Rangers | | 2:2 |
| |
Scottish League Cup 1963, Group 5 |
| 10.08.1963 | | Stirling Albion | – | Alloa Athletic | | 3:3 |
| |
Scottish League Cup 1962, Group 8 |
| 11.08.1962 | | Stirling Albion | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1960, Group 8 |
| 31.08.1960 | | Stirling Albion | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1959, Group 3 |
| 29.08.1959 | | Hearts | – | Stirling Albion | | 2:2 |
| |
Scottish League Cup 1959, Group 3 |
| 12.08.1959 | | Stirling Albion | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1956, Group 7 |
| 15.08.1956 | | Stirling Albion | – | St. Johnstone | | 0:0 |
| |
Scottish League Cup 1955, Group 6 |
| 03.09.1955 | | Ayr United | – | Stirling Albion | | 2:2 |
| |
Scottish League Cup 1953, Group 4 |
| 29.08.1953 | | Stirling Albion | – | Clyde | | 3:3 |
| |
Scottish League Cup 1951, Group 2 |
| 01.09.1951 | | Stirling Albion | – | Hibernian | | 1:1 |
| |
Scottish League Cup 1951, Group 2 |
| 29.08.1951 | | Partick Thistle | – | Stirling Albion | | 0:0 |
| |
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 | | Stirling Albion | – | Queen's Park | | 2:2 |
| |
Scottish League Cup 1948, Group 5 |
| 11.09.1948 | | Dunfermline Athletic | – | Stirling Albion | | 1:1 |
| |
