Scottish League Cup 2023/24, Group H |
 | 22.07.2023 |  | Cowdenbeath | – | Montrose | | 1:1 (0:0),
pen. 4:5 |
| Cowdenbeath |
Scottish League Cup 2021/22, Group C |
| 13.07.2021 | | Forfar Athletic | – | Montrose | | 0:0,
pen. 5:4 |
| Forfar |
Scottish League Cup 2020/21, Group D |
| 07.10.2020 | | Montrose | – | Ross County | | 3:3 (0:2),
pen. 4:5 |
| Montrose |
Scottish League Cup 2019/20, Group B |
| 27.07.2019 | | Brechin City | – | Montrose | | 1:1 (0:0),
pen. 2:4 |
| Brechin |
Scottish League Cup 1994, Second Round |
| 16.08.1994 | | Falkirk | – | Montrose | | 1:1 aet,
pen. 5:4 |
| |
Scottish League Cup 1994, First Round |
| 09.08.1994 | | Berwick Rangers | – | Montrose | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 1982, Group 9 |
| 18.08.1982 | | Stenhousemuir | – | Montrose | | 2:2 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | Montrose | – | Hibernian | | 1:1 |
| |
Scottish League Cup 1978/79, Quarterfinal |
| 08.11.1978 | | Montrose | – | Celtic | | 1:1 |
| |
Scottish League Cup 1978/79, Second Round |
| 28.08.1978 | | Montrose | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1976, Group 4 |
| 01.09.1976 | | Hibernian | – | Montrose | | 0:0 |
| |
Scottish League Cup 1976, Group 4 |
| 18.08.1976 | | St. Johnstone | – | Montrose | | 0:0 |
| |
Scottish League Cup 1975, Group 6 |
| 23.08.1975 | | East Fife | – | Montrose | | 1:1 |
| |
Scottish League Cup 1975, Group 6 |
| 13.08.1975 | | Montrose | – | St. Mirren | | 1:1 |
| |
Scottish League Cup 1974, Group 6 |
| 28.08.1974 | | Montrose | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1974, Group 6 |
| 14.08.1974 | | Montrose | – | Queen's Park | | 0:0 |
| |
Scottish League Cup 1973, Group 7 |
| 18.08.1973 | | Montrose | – | Airdrieonians | | 2:2 |
| |
Scottish League Cup 1973, Group 7 |
| 11.08.1973 | | Montrose | – | Clyde | | 2:2 |
| |
Scottish League Cup 1971, Group 8 |
| 21.08.1971 | | Montrose | – | Stranraer | | 2:2 |
| |
Scottish League Cup 1971, Group 8 |
| 18.08.1971 | | Montrose | – | Albion Rovers | | 1:1 |
| |
Scottish League Cup 1969, Group 5 |
| 23.08.1969 | | Montrose | – | Albion Rovers | | 1:1 |
| |
Scottish League Cup 1966, Quarterfinal |
| 14.09.1966 | | Montrose | – | Airdrieonians | | 3:3 |
| |
Scottish League Cup 1966, Group 8 |
| 03.09.1966 | | Montrose | – | Albion Rovers | | 2:2 |
| |
Scottish League Cup 1966, Group 8 |
| 20.08.1966 | | Albion Rovers | – | Montrose | | 0:0 |
| |
Scottish League Cup 1963, Group 9 |
| 24.08.1963 | | Brechin City | – | Montrose | | 2:2 |
| |
Scottish League Cup 1962, Group 7 |
| 01.09.1962 | | Montrose | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1962, Group 7 |
| 25.08.1962 | | Queen's Park | – | Montrose | | 1:1 |
| |
Scottish League Cup 1961, Group 6 |
| 12.08.1961 | | Montrose | – | Hamilton Academical | | 2:2 |
| |
Scottish League Cup 1959, Group 9 |
| 12.08.1959 | | Montrose | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1958, Group 8 |
| 09.08.1958 | | Montrose | – | Forfar Athletic | | 2:2 |
| |
