Scottish League Cup 2023/24, Group H |
 | 15.07.2023 |  | Montrose | – | St. Mirren | | 1:0 (0:0) |
| Montrose |
Scottish League Cup 2022/23, Group B |
| 12.07.2022 | | Fraserburgh | – | Montrose | | 2:4 (0:3) |
| Fraserburgh |
Scottish League Cup 2021/22, Group C |
| 10.07.2021 | | Montrose | – | Brora Rangers | | 3:0 (2:0) |
| Montrose |
Scottish League Cup 2019/20, Group B |
| 16.07.2019 | | Montrose | – | St. Johnstone | | 1:0 (0:0) |
| Montrose |
Scottish League Cup 2018/19, Group B |
| 17.07.2018 | | Montrose | – | East Fife | | 1:0 (0:0) |
| Montrose |
Scottish League Cup 2018/19, Group B |
| 14.07.2018 | | Falkirk | – | Montrose | | 0:1 (0:1) |
| Falkirk |
Scottish League Cup 2017/18, Group D |
| 25.07.2017 | | Montrose | – | Alloa Athletic | | 2:1 (1:0) |
| Montrose |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Arbroath | – | Montrose | | 0:1 (0:0) |
| Arbroath |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Montrose | – | Cowdenbeath | | 2:1 (2:0) |
| Montrose |
Scottish League Cup 2007/08, First Round |
| 08.08.2007 | | Stranraer | – | Montrose | | 1:2 (0:2) |
| Montrose |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | Montrose | – | Stirling Albion | | 2:0 (0:0) |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | Montrose | – | Berwick Rangers | | 1:0 |
| |
Scottish League Cup 1989, First Round |
| 09.08.1989 | | Cowdenbeath | – | Montrose | | 0:4 aet |
| |
Scottish League Cup 1986, Second Round |
| 19.08.1986 | | Hearts | – | Montrose | | 0:2 |
| |
Scottish League Cup 1983/84, First Round |
| 17.08.1983 | | East Stirlingshire | – | Montrose | | 1:2 |
| |
Scottish League Cup 1983/84, First Round |
| 13.08.1983 | | Montrose | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1982, Group 9 |
| 28.08.1982 | | Albion Rovers | – | Montrose | | 1:2 |
| |
Scottish League Cup 1982, Group 9 |
| 21.08.1982 | | Montrose | – | Stranraer | | 1:0 |
| |
Scottish League Cup 1982, Group 9 |
| 14.08.1982 | | Cowdenbeath | – | Montrose | | 0:1 |
| |
Scottish League Cup 1981, Group 8 |
| 22.08.1981 | | East Stirlingshire | – | Montrose | | 1:2 |
| |
Scottish League Cup 1981, Group 8 |
| 08.08.1981 | | Montrose | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1978/79, Third Round |
| 11.10.1978 | | Montrose | – | Raith Rovers | | 5:1 |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | East Stirlingshire | – | Montrose | | 0:2 aet |
| |
Scottish League Cup 1978/79, First Round |
| 23.08.1978 | | Queen of the South | – | Montrose | | 0:1 |
| |
Scottish League Cup 1978/79, First Round |
| 16.08.1978 | | Montrose | – | Queen of the South | | 4:0 |
| |
Scottish League Cup 1976, Group 4 |
| 25.08.1976 | | Montrose | – | St. Johnstone | | 5:1 |
| |
Scottish League Cup 1975, Quarterfinal |
| 24.09.1975 | | Montrose | – | Hibernian | | 3:1 aet |
| |
Scottish League Cup 1975, Group 6 |
| 27.08.1975 | | Montrose | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1975, Group 6 |
| 20.08.1975 | | St. Mirren | – | Montrose | | 1:2 |
| |
Scottish League Cup 1975, Group 6 |
| 16.08.1975 | | Montrose | – | East Fife | | 4:0 |
| |
Scottish League Cup 1974, Group 6 |
| 24.08.1974 | | Montrose | – | Stranraer | | 2:0 |
| |
Scottish League Cup 1974, Group 6 |
| 21.08.1974 | | Queen's Park | – | Montrose | | 2:3 |
| |
Scottish League Cup 1974, Group 6 |
| 17.08.1974 | | Stranraer | – | Montrose | | 2:4 |
| |
Scottish League Cup 1973, Group 7 |
| 22.08.1973 | | Montrose | – | Alloa Athletic | | 3:0 |
| |
Scottish League Cup 1972, Group 5 |
| 23.08.1972 | | Montrose | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1972, Group 5 |
| 16.08.1972 | | Raith Rovers | – | Montrose | | 1:2 |
| |
Scottish League Cup 1971, Group 8 |
| 01.09.1971 | | Stranraer | – | Montrose | | 2:4 |
| |
Scottish League Cup 1971, Group 8 |
| 25.08.1971 | | Albion Rovers | – | Montrose | | 0:2 |
| |
Scottish League Cup 1970, Group 7 |
| 26.08.1970 | | Montrose | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1970, Group 7 |
| 22.08.1970 | | Montrose | – | Raith Rovers | | 4:1 |
| |
Scottish League Cup 1970, Group 7 |
| 15.08.1970 | | East Stirlingshire | – | Montrose | | 1:2 |
| |
Scottish League Cup 1970, Group 7 |
| 12.08.1970 | | Montrose | – | Cowdenbeath | | 3:2 |
| |
Scottish League Cup 1969, Group 5 |
| 09.08.1969 | | Albion Rovers | – | Montrose | | 0:1 |
| |
Scottish League Cup 1968/69, Group 7 |
| 28.08.1968 | | Montrose | – | Motherwell | | 2:1 |
| |
Scottish League Cup 1968/69, Group 7 |
| 14.08.1968 | | Motherwell | – | Montrose | | 1:2 |
| |
Scottish League Cup 1967, Group 6 |
| 02.09.1967 | | Montrose | – | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1966, Group 8 |
| 27.08.1966 | | Montrose | – | Hamilton Academical | | 2:0 |
| |
Scottish League Cup 1966, Group 8 |
| 17.08.1966 | | Montrose | – | Alloa Athletic | | 2:1 |
| |
Scottish League Cup 1966, Group 8 |
| 13.08.1966 | | Hamilton Academical | – | Montrose | | 1:3 |
| |
Scottish League Cup 1965, Group 9 |
| 18.08.1965 | | Montrose | – | Brechin City | | 2:0 |
| |
Scottish League Cup 1963, Group 9 |
| 14.08.1963 | | Forfar Athletic | – | Montrose | | 1:2 |
| |
Scottish League Cup 1963, Group 9 |
| 10.08.1963 | | Montrose | – | Berwick Rangers | | 3:0 |
| |
Scottish League Cup 1962, Group 7 |
| 15.08.1962 | | East Fife | – | Montrose | | 0:5 |
| |
Scottish League Cup 1962, Group 7 |
| 11.08.1962 | | Montrose | – | Queen's Park | | 3:1 |
| |
Scottish League Cup 1961, Group 6 |
| 02.09.1961 | | Montrose | – | Clyde | | 4:0 |
| |
Scottish League Cup 1961, Group 6 |
| 30.08.1961 | | Montrose | – | Stenhousemuir | | 4:0 |
| |
Scottish League Cup 1961, Group 6 |
| 16.08.1961 | | Stenhousemuir | – | Montrose | | 1:4 |
| |
Scottish League Cup 1960, Group 5 |
| 27.08.1960 | | Montrose | – | Queen's Park | | 2:1 |
| |
Scottish League Cup 1960, Group 5 |
| 17.08.1960 | | Montrose | – | Albion Rovers | | 3:1 |
| |
Scottish League Cup 1960, Group 5 |
| 13.08.1960 | | Queen's Park | – | Montrose | | 0:2 |
| |
Scottish League Cup 1957, Supplementary Round |
| 02.09.1957 | | Montrose | – | Hamilton Academical | | 1:0 |
| |
Scottish League Cup 1957, Group 9 |
| 31.08.1957 | | Montrose | – | Alloa Athletic | | 3:1 |
| |
Scottish League Cup 1957, Group 9 |
| 24.08.1957 | | Berwick Rangers | – | Montrose | | 1:3 |
| |
Scottish League Cup 1957, Group 9 |
| 14.08.1957 | | Montrose | – | Forfar Athletic | | 4:1 |
| |
Scottish League Cup 1955, Group 9 |
| 03.09.1955 | | Berwick Rangers | – | Montrose | | 1:2 |
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