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 |
| |