Scottish League Cup 2000/01, First Round |
 | 08.08.2000 |  | East Stirlingshire | – | Hamilton Academical | | 2:1 |
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Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Clydebank | – | East Stirlingshire | | 1:2 |
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Scottish League Cup 1997, First Round |
| 02.08.1997 | | East Stirlingshire | – | Stranraer | | 3:1 |
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Scottish League Cup 1995, First Round |
| 05.08.1995 | | Clyde | – | East Stirlingshire | | 1:2 |
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Scottish League Cup 1993, First Round |
| 04.08.1993 | | Montrose | – | East Stirlingshire | | 0:1 |
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Scottish League Cup 1987, First Round |
| 11.08.1987 | | Stenhousemuir | – | East Stirlingshire | | 1:3 aet |
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Scottish League Cup 1986, First Round |
| 13.08.1986 | | Stranraer | – | East Stirlingshire | | 0:2 |
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Scottish League Cup 1982, Group 7 |
| 21.08.1982 | | East Fife | – | East Stirlingshire | | 0:1 |
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Scottish League Cup 1976, Group 7 |
| 01.09.1976 | | East Stirlingshire | – | Cowdenbeath | | 4:0 |
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Scottish League Cup 1975, Group 7 |
| 09.08.1975 | | Berwick Rangers | – | East Stirlingshire | | 1:2 |
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Scottish League Cup 1974, Group 9 |
| 28.08.1974 | | Stenhousemuir | – | East Stirlingshire | | 0:2 |
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Scottish League Cup 1974, Group 9 |
| 24.08.1974 | | East Stirlingshire | – | Brechin City | | 3:2 |
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Scottish League Cup 1974, Group 9 |
| 14.08.1974 | | East Stirlingshire | – | Meadowbank Thistle | | 3:1 |
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Scottish League Cup 1973, Group 5 |
| 18.08.1973 | | East Stirlingshire | – | Hamilton Academical | | 2:0 |
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Scottish League Cup 1973, Group 5 |
| 15.08.1973 | | Queen's Park | – | East Stirlingshire | | 0:1 |
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Scottish League Cup 1973, Group 5 |
| 11.08.1973 | | East Stirlingshire | – | Kilmarnock | | 3:2 |
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Scottish League Cup 1971, Group 9 |
| 25.08.1971 | | Brechin City | – | East Stirlingshire | | 1:4 |
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Scottish League Cup 1970, Group 7 |
| 12.08.1970 | | East Stirlingshire | – | Raith Rovers | | 2:0 |
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Scottish League Cup 1969, Group 6 |
| 23.08.1969 | | East Stirlingshire | – | Queen of the South | | 2:0 |
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Scottish League Cup 1968/69, Group 9 |
| 17.08.1968 | | East Stirlingshire | – | Stenhousemuir | | 3:0 |
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Scottish League Cup 1965, Group 8 |
| 04.09.1965 | | East Stirlingshire Clydebank | – | East Fife | | 6:2 |
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Scottish League Cup 1965, Group 8 |
| 28.08.1965 | | East Stirlingshire Clydebank | – | Dumbarton | | 1:0 |
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Scottish League Cup 1965, Group 8 |
| 18.08.1965 | | East Stirlingshire Clydebank | – | Alloa Athletic | | 1:0 |
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Scottish League Cup 1964, Group 6 |
| 22.08.1964 | | Stenhousemuir | – | East Stirlingshire Clydebank | | 1:2 |
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Scottish League Cup 1963, Group 7 |
| 31.08.1963 | | East Stirlingshire | – | Hamilton Academical | | 1:0 |
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Scottish League Cup 1963, Group 7 |
| 28.08.1963 | | East Stirlingshire | – | St. Johnstone | | 2:1 |
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Scottish League Cup 1963, Group 7 |
| 24.08.1963 | | Queen's Park | – | East Stirlingshire | | 0:1 |
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Scottish League Cup 1963, Group 7 |
| 17.08.1963 | | Hamilton Academical | – | East Stirlingshire | | 2:3 |
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Scottish League Cup 1963, Group 7 |
| 10.08.1963 | | East Stirlingshire | – | Queen's Park | | 2:0 |
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Scottish League Cup 1962, Group 5 |
| 18.08.1962 | | East Stirlingshire | – | Berwick Rangers | | 3:2 |
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Scottish League Cup 1962, Group 5 |
| 11.08.1962 | | East Stirlingshire | – | Ayr United | | 4:1 |
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Scottish League Cup 1961, Group 9 |
| 26.08.1961 | | East Stirlingshire | – | Forfar Athletic | | 1:0 |
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Scottish League Cup 1961, Group 9 |
| 19.08.1961 | | East Stirlingshire | – | Morton | | 4:1 |
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Scottish League Cup 1960, Group 9 |
| 27.08.1960 | | East Stirlingshire | – | East Fife | | 4:1 |
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Scottish League Cup 1959, Group 9 |
| 15.08.1959 | | East Stirlingshire | – | Montrose | | 5:1 |
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Scottish League Cup 1957, Group 9 |
| 31.08.1957 | | East Stirlingshire | – | Berwick Rangers | | 5:1 |
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Scottish League Cup 1957, Group 9 |
| 10.08.1957 | | East Stirlingshire | – | Montrose | | 3:1 |
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Scottish League Cup 1956, Group 9 |
| 01.09.1956 | | Forfar Athletic | – | East Stirlingshire | | 0:1 |
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Scottish League Cup 1956, Group 9 |
| 15.08.1956 | | East Stirlingshire | – | Montrose | | 3:0 |
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Scottish League Cup 1955, Group 9 |
| 27.08.1955 | | East Stirlingshire | – | Berwick Rangers | | 3:2 |
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Scottish League Cup 1955, Group 9 |
| 20.08.1955 | | East Stirlingshire | – | Stranraer | | 5:2 |
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Scottish League Cup 1955, Group 9 |
| 17.08.1955 | | Montrose | – | East Stirlingshire | | 2:5 |
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Scottish League Cup 1948, Group 6 |
| 11.09.1948 | | East Stirlingshire | – | Kilmarnock | | 2:1 |
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