Scottish League Cup 2023/24, Group H |
| 29.07.2023 | | Arbroath | | Montrose | | 3:0 (1:0) |
| Arbroath |
Scottish League Cup 2023/24, Group H |
| 18.07.2023 | | Montrose | | Forfar Athletic | | 1:2 (0:2) |
| Montrose |
Scottish League Cup 2022/23, Group B |
| 23.07.2022 | | Partick Thistle | | Montrose | | 4:2 (2:0) |
| Glasgow |
Scottish League Cup 2022/23, Group B |
| 19.07.2022 | | Montrose | | Stenhousemuir | | 0:2 (0:0) |
| Montrose |
Scottish League Cup 2022/23, Group B |
| 16.07.2022 | | Montrose | | Kilmarnock | | 0:3 (0:1) |
| Montrose |
Scottish League Cup 2021/22, Group C |
| 24.07.2021 | | Ross County | | Montrose | | 4:1 (2:0) |
| Dingwall |
Scottish League Cup 2021/22, Group C |
| 21.07.2021 | | Montrose | | Dundee | | 0:2 (0:0) |
| Montrose |
Scottish League Cup 2020/21, Group D |
| 10.11.2020 | | Stirling Albion | | Montrose | | 2:1 (2:1) |
| Stirling |
Scottish League Cup 2020/21, Group D |
| 13.10.2020 | | Montrose | | Elgin City | | 0:2 (0:2) |
| Montrose |
Scottish League Cup 2020/21, Group D |
| 10.10.2020 | | Arbroath | | Montrose | | 3:1 (2:1) |
| Arbroath |
Scottish League Cup 2019/20, Group B |
| 20.07.2019 | | Montrose | | Forfar Athletic | | 1:4 (1:2) |
| Montrose |
Scottish League Cup 2019/20, Group B |
| 13.07.2019 | | Ross County | | Montrose | | 4:1 (2:0) |
| Dingwall |
Scottish League Cup 2018/19, Group B |
| 25.07.2018 | | Forfar Athletic | | Montrose | | 3:1 (2:0) |
| Forfar |
Scottish League Cup 2018/19, Group B |
| 21.07.2018 | | Montrose | | St. Johnstone | | 0:1 (0:1) |
| Montrose |
Scottish League Cup 2017/18, Group D |
| 22.07.2017 | | Arbroath | | Montrose | | 4:0 (1:0) |
| Arbroath |
Scottish League Cup 2017/18, Group D |
| 18.07.2017 | | Montrose | | Ross County | | 0:6 (0:4) |
| Montrose |
Scottish League Cup 2017/18, Group D |
| 15.07.2017 | | Hibernian | | Montrose | | 4:0 (2:0) |
| Edinburgh |
Scottish League Cup 2016/17, First Round, Group D |
| 27.07.2016 | | Cove Rangers | | Montrose | | 3:0 (1:0) |
| Forfar |
Scottish League Cup 2016/17, First Round, Group D |
| 23.07.2016 | | Montrose | | Alloa Athletic | | 0:2 (0:1) |
| Montrose |
Scottish League Cup 2016/17, First Round, Group D |
| 19.07.2016 | | Raith Rovers | | Montrose | | 2:1 (1:0) |
| Kirkcaldy |
Scottish League Cup 2016/17, First Round, Group D |
| 16.07.2016 | | Montrose | | Ross County | | 0:1 (0:0) |
| Montrose |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | Hibernian | | Montrose | | 3:0 (1:0) |
| Edinburgh |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Montrose | | Falkirk | | 1:3 (1:2) |
| Montrose |
Scottish League Cup 2013/14, Second Round |
| 27.08.2013 | | Greenock Morton | | Montrose | | 4:0 (0:0) |
| Greenock |
Scottish League Cup 2012/13, Second Round |
| 28.08.2012 | | Dunfermline Athletic | | Montrose | | 3:0 (2:0) |
| Dunfermline |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | Montrose | | Raith Rovers | | 1:4 (1:1) |
| Montrose |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Dundee | | Montrose | | 3:0 (1:0) |
| Dundee |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Ross County | | Montrose | | 5:0 (1:0) |
| Dingwall |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Montrose | | Cowdenbeath | | 0:2 (0:1) |
| Montrose |
Scottish League Cup 2007/08, Second Round |
| 28.08.2007 | | Montrose | | Falkirk | | 1:2 (0:1) |
| Montrose |
Scottish League Cup 2006/07, First Round |
| 09.08.2006 | | Montrose | | Peterhead | | 1:3 aet (1:0, 1:1) |
| Montrose |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | Montrose | | Clyde | | 0:1 (0:1) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Falkirk | | Montrose | | 4:1 (2:0) |
| |
Scottish League Cup 2003/04, Second Round |
| 23.09.2003 | | Hibernian | | Montrose | | 9:0 (4:0) |
| |
Scottish League Cup 2002/03, First Round |
| 10.09.2002 | | Cowdenbeath | | Montrose | | 3:2 (0:0) |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | Raith Rovers | | Montrose | | 1:0 |
| |
Scottish League Cup 2000/01, Second Round |
| 23.08.2000 | | Dundee | | Montrose | | 3:0 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Montrose | | Hamilton Academical | | 1:2 |
| |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Ross County | | Montrose | | 4:1 |
| |
Scottish League Cup 1997, First Round |
| 02.08.1997 | | Ross County | | Montrose | | 2:1 |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | Brechin City | | Montrose | | 3:0 |
| |
Scottish League Cup 1995, First Round |
| 05.08.1995 | | Montrose | | Livingston | | 0:2 |
| |
Scottish League Cup 1993, First Round |
| 04.08.1993 | | Montrose | | East Stirlingshire | | 0:1 |
| |
Scottish League Cup 1992, Second Round |
| 12.08.1992 | | Montrose | | Dunfermline Athletic | | 0:6 |
| |
Scottish League Cup 1991, Second Round |
| 20.08.1991 | | Dundee United | | Montrose | | 3:2 |
| |
Scottish League Cup 1990, First Round |
| 15.08.1990 | | Montrose | | Queen of the South | | 1:2 |
| |
Scottish League Cup 1989, Second Round |
| 16.08.1989 | | Hearts | | Montrose | | 3:0 |
| |
Scottish League Cup 1988, First Round |
| 10.08.1988 | | Brechin City | | Montrose | | 3:1 |
| |
Scottish League Cup 1987, Second Round |
| 18.08.1987 | | Hibernian | | Montrose | | 3:2 |
| |
Scottish League Cup 1986, Third Round |
| 27.08.1986 | | Dundee | | Montrose | | 4:0 |
| |
Scottish League Cup 1985, Second Round |
| 20.08.1985 | | Montrose | | Hearts | | 1:3 |
| |
Scottish League Cup 1984, First Round |
| 14.08.1984 | | Albion Rovers | | Montrose | | 2:0 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | Dundee | | Montrose | | 4:1 |
| |
Scottish League Cup 1983/84, Second Round |
| 23.08.1983 | | Montrose | | Dundee | | 1:3 |
| |
Scottish League Cup 1982, Group 9 |
| 25.08.1982 | | Montrose | | Meadowbank Thistle | | 0:1 |
| |
Scottish League Cup 1981, Group 8 |
| 26.08.1981 | | Hamilton Academical | | Montrose | | 4:2 |
| |
Scottish League Cup 1981, Group 8 |
| 19.08.1981 | | Montrose | | Dunfermline Athletic | | 0:1 |
| |
Scottish League Cup 1981, Group 8 |
| 15.08.1981 | | Montrose | | Hamilton Academical | | 1:2 |
| |
Scottish League Cup 1981, Group 8 |
| 12.08.1981 | | Dunfermline Athletic | | Montrose | | 2:1 |
| |
Scottish League Cup 1980, Second Round |
| 30.08.1980 | | Montrose | | Hearts | | 1:3 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Hearts | | Montrose | | 2:1 |
| |
Scottish League Cup 1979, Second Round |
| 29.08.1979 | | Hibernian | | Montrose | | 2:1 |
| |
Scottish League Cup 1978/79, Quarterfinal |
| 15.11.1978 | | Celtic | | Montrose | | 3:1 |
| |
Scottish League Cup 1978/79, Third Round |
| 04.10.1978 | | Raith Rovers | | Montrose | | 3:0 |
| |
Scottish League Cup 1977/78, First Round |
| 24.08.1977 | | Dundee | | Montrose | | 1:0 |
| |
Scottish League Cup 1977/78, First Round |
| 17.08.1977 | | Montrose | | Dundee | | 1:3 |
| |
Scottish League Cup 1976, Group 4 |
| 28.08.1976 | | Montrose | | Rangers | | 0:3 |
| |
Scottish League Cup 1976, Group 4 |
| 21.08.1976 | | Rangers | | Montrose | | 4:0 |
| |
Scottish League Cup 1976, Group 4 |
| 14.08.1976 | | Montrose | | Hibernian | | 0:1 |
| |
Scottish League Cup 1975, Semifinal |
| 06.10.1975 | | Rangers | | Montrose | | 5:1 |
| |
Scottish League Cup 1975, Quarterfinal |
| 10.09.1975 | | Hibernian | | Montrose | | 1:0 |
| |
Scottish League Cup 1975, Group 6 |
| 09.08.1975 | | Raith Rovers | | Montrose | | 2:1 |
| |
Scottish League Cup 1974, Group 6 |
| 10.08.1974 | | Kilmarnock | | Montrose | | 2:0 |
| |
Scottish League Cup 1973, Group 7 |
| 29.08.1973 | | Clyde | | Montrose | | 2:1 |
| |
Scottish League Cup 1973, Group 7 |
| 25.08.1973 | | Airdrieonians | | Montrose | | 6:4 |
| |
Scottish League Cup 1973, Group 7 |
| 15.08.1973 | | Alloa Athletic | | Montrose | | 3:1 |
| |
Scottish League Cup 1972, Group 5 |
| 30.08.1972 | | Montrose | | St. Johnstone | | 0:3 |
| |
Scottish League Cup 1972, Group 5 |
| 26.08.1972 | | Falkirk | | Montrose | | 3:0 |
| |
Scottish League Cup 1972, Group 5 |
| 19.08.1972 | | St. Johnstone | | Montrose | | 4:1 |
| |
Scottish League Cup 1972, Group 5 |
| 12.08.1972 | | Montrose | | Falkirk | | 3:4 |
| |
Scottish League Cup 1971, Group 8 |
| 28.08.1971 | | Montrose | | St. Mirren | | 0:1 |
| |
Scottish League Cup 1971, Group 8 |
| 14.08.1971 | | St. Mirren | | Montrose | | 4:1 |
| |
Scottish League Cup 1970, Group 7 |
| 19.08.1970 | | Cowdenbeath | | Montrose | | 3:0 |
| |
Scottish League Cup 1970, Group 7 |
| 08.08.1970 | | Raith Rovers | | Montrose | | 1:0 |
| |
Scottish League Cup 1969, Group 5 |
| 27.08.1969 | | Montrose | | East Fife | | 1:3 |
| |
Scottish League Cup 1969, Group 5 |
| 20.08.1969 | | Motherwell | | Montrose | | 3:2 |
| |
Scottish League Cup 1969, Group 5 |
| 16.08.1969 | | East Fife | | Montrose | | 4:1 |
| |
Scottish League Cup 1969, Group 5 |
| 13.08.1969 | | Montrose | | Motherwell | | 1:4 |
| |
Scottish League Cup 1968/69, Group 7 |
| 31.08.1968 | | Hamilton Academical | | Montrose | | 2:0 |
| |
Scottish League Cup 1968/69, Group 7 |
| 24.08.1968 | | St. Mirren | | Montrose | | 1:0 |
| |
Scottish League Cup 1968/69, Group 7 |
| 17.08.1968 | | Montrose | | Hamilton Academical | | 0:2 |
| |
Scottish League Cup 1968/69, Group 7 |
| 10.08.1968 | | Montrose | | St. Mirren | | 1:2 |
| |
Scottish League Cup 1967, Group 6 |
| 30.08.1967 | | Montrose | | Queen's Park | | 0:1 |
| |
Scottish League Cup 1967, Group 6 |
| 26.08.1967 | | Hamilton Academical | | Montrose | | 3:1 |
| |
Scottish League Cup 1967, Group 6 |
| 19.08.1967 | | Cowdenbeath | | Montrose | | 3:0 |
| |
Scottish League Cup 1967, Group 6 |
| 16.08.1967 | | Queen's Park | | Montrose | | 2:1 |
| |
Scottish League Cup 1967, Group 6 |
| 12.08.1967 | | Montrose | | Hamilton Academical | | 2:3 |
| |
Scottish League Cup 1966, Quarterfinal |
| 21.09.1966 | | Airdrieonians | | Montrose | | 5:1 |
| |
Scottish League Cup 1966, Group 8 |
| 31.08.1966 | | Alloa Athletic | | Montrose | | 1:0 |
| |
Scottish League Cup 1965, Group 9 |
| 28.08.1965 | | Montrose | | Stenhousemuir | | 1:3 |
| |
Scottish League Cup 1965, Group 9 |
| 21.08.1965 | | Ayr United | | Montrose | | 5:0 |
| |
Scottish League Cup 1965, Group 9 |
| 14.08.1965 | | Forfar Athletic | | Montrose | | 4:1 |
| |
Scottish League Cup 1964, Group 5 |
| 29.08.1964 | | Montrose | | East Fife | | 0:5 |
| |
Scottish League Cup 1964, Group 5 |
| 26.08.1964 | | Raith Rovers | | Montrose | | 7:0 |
| |
Scottish League Cup 1964, Group 5 |
| 22.08.1964 | | Montrose | | Queen of the South | | 1:6 |
| |
Scottish League Cup 1964, Group 5 |
| 15.08.1964 | | East Fife | | Montrose | | 4:2 |
| |
Scottish League Cup 1964, Group 5 |
| 12.08.1964 | | Montrose | | Raith Rovers | | 2:4 |
| |
Scottish League Cup 1964, Group 5 |
| 08.08.1964 | | Queen of the South | | Montrose | | 2:0 |
| |
Scottish League Cup 1963, Group 9 |
| 17.08.1963 | | Montrose | | Stenhousemuir | | 2:3 |
| |
Scottish League Cup 1962, Group 7 |
| 29.08.1962 | | Montrose | | East Fife | | 0:1 |
| |
Scottish League Cup 1962, Group 7 |
| 18.08.1962 | | Queen of the South | | Montrose | | 2:1 |
| |
Scottish League Cup 1961, Group 6 |
| 26.08.1961 | | Hamilton Academical | | Montrose | | 2:0 |
| |
Scottish League Cup 1961, Group 6 |
| 19.08.1961 | | Clyde | | Montrose | | 3:2 |
| |
Scottish League Cup 1960, Group 5 |
| 03.09.1960 | | Montrose | | Queen of the South | | 1:2 |
| |
Scottish League Cup 1960, Group 5 |
| 31.08.1960 | | Albion Rovers | | Montrose | | 2:1 |
| |
Scottish League Cup 1960, Group 5 |
| 20.08.1960 | | Queen of the South | | Montrose | | 5:2 |
| |
Scottish League Cup 1959, Group 9 |
| 29.08.1959 | | Stranraer | | Montrose | | 4:2 |
| |
Scottish League Cup 1959, Group 9 |
| 22.08.1959 | | Montrose | | Queen's Park | | 0:2 |
| |
Scottish League Cup 1959, Group 9 |
| 15.08.1959 | | East Stirlingshire | | Montrose | | 5:1 |
| |
Scottish League Cup 1958, Group 8 |
| 30.08.1958 | | Hamilton Academical | | Montrose | | 3:0 |
| |
Scottish League Cup 1958, Group 8 |
| 27.08.1958 | | Montrose | | Ayr United | | 1:2 |
| |
Scottish League Cup 1958, Group 8 |
| 23.08.1958 | | Forfar Athletic | | Montrose | | 4:1 |
| |
Scottish League Cup 1958, Group 8 |
| 16.08.1958 | | Montrose | | Hamilton Academical | | 2:3 |
| |
Scottish League Cup 1958, Group 8 |
| 13.08.1958 | | Ayr United | | Montrose | | 7:1 |
| |
Scottish League Cup 1957, Supplementary Round |
| 04.09.1957 | | Hamilton Academical | | Montrose | | 3:0 |
| |
Scottish League Cup 1957, Group 9 |
| 10.08.1957 | | East Stirlingshire | | Montrose | | 3:1 |
| |
Scottish League Cup 1956, Group 9 |
| 01.09.1956 | | Arbroath | | Montrose | | 6:1 |
| |
Scottish League Cup 1956, Group 9 |
| 25.08.1956 | | Montrose | | Albion Rovers | | 3:5 |
| |
Scottish League Cup 1956, Group 9 |
| 15.08.1956 | | East Stirlingshire | | Montrose | | 3:0 |
| |
Scottish League Cup 1956, Group 9 |
| 11.08.1956 | | Montrose | | Forfar Athletic | | 2:3 |
| |
Scottish League Cup 1955, Group 9 |
| 20.08.1955 | | Montrose | | Dumbarton | | 0:2 |
| |
Scottish League Cup 1955, Group 9 |
| 17.08.1955 | | Montrose | | East Stirlingshire | | 2:5 |
| |
Scottish League Cup 1955, Group 9 |
| 13.08.1955 | | Stranraer | | Montrose | | 3:2 |
| |