Scottish League Cup 2023/24, Second Round |
 | 19.08.2023 |  | Airdrieonians | – | Ross County | | 3:4 aet
(1:3, 3:3) |
| Airdrie |
Scottish League Cup 2023/24, Group D |
| 26.07.2023 | | Edinburgh | – | Ross County | | 1:3 (0:1) |
| Edinburgh |
Scottish League Cup 2023/24, Group D |
| 22.07.2023 | | Ross County | – | Greenock Morton | | 2:1 (0:1) |
| Dingwall |
Scottish League Cup 2023/24, Group D |
| 15.07.2023 | | Stranraer | – | Ross County | | 1:5 (0:2) |
| Stranraer |
Scottish League Cup 2022/23, Group C |
| 23.07.2022 | | Ross County | – | East Fife | | 7:0 (2:0) |
| Dingwall |
Scottish League Cup 2022/23, Group C |
| 19.07.2022 | | Alloa Athletic | – | Ross County | | 0:2 (0:1) |
| Alloa |
Scottish League Cup 2022/23, Group C |
| 16.07.2022 | | Ross County | – | Dunfermline Athletic | | 1:0 (0:0) |
| Dingwall |
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 | | Brora Rangers | – | Ross County | | 0:1 (0:0) |
| Brora |
Scottish League Cup 2020/21, Second round |
| 29.11.2020 | | Celtic | – | Ross County | | 0:2 (0:1) |
| Glasgow |
Scottish League Cup 2020/21, Group D |
| 14.11.2020 | | Ross County | – | Stirling Albion | | 3:0 (1:0) |
| Dingwall |
Scottish League Cup 2020/21, Group D |
| 10.11.2020 | | Elgin City | – | Ross County | | 1:4 (0:2) |
| Elgin |
Scottish League Cup 2020/21, Group D |
| 13.10.2020 | | Ross County | – | Arbroath | | 2:1 (0:0) |
| Dingwall |
Scottish League Cup 2019/20, Group B |
| 24.07.2019 | | Ross County | – | Forfar Athletic | | 2:0 (1:0) |
| Dingwall |
Scottish League Cup 2019/20, Group B |
| 21.07.2019 | | St. Johnstone | – | Ross County | | 1:2 (1:2) |
| Perth |
Scottish League Cup 2019/20, Group B |
| 16.07.2019 | | Brechin City | – | Ross County | | 0:4 (0:2) |
| Brechin |
Scottish League Cup 2019/20, Group B |
| 13.07.2019 | | Ross County | – | Montrose | | 4:1 (2:0) |
| Dingwall |
Scottish League Cup 2018/19, Group A |
| 28.07.2018 | | Alloa Athletic | – | Ross County | | 0:2 (0:0) |
| Alloa |
Scottish League Cup 2018/19, Group A |
| 17.07.2018 | | Ross County | – | Dundee United | | 1:0 (0:0) |
| Dingwall |
Scottish League Cup 2018/19, Group A |
| 14.07.2018 | | Ross County | – | Elgin City | | 2:0 (0:0) |
| Dingwall |
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 | | Ross County | – | Alloa Athletic | | 2:0 (1:0) |
| Dingwall |
Scottish League Cup 2016/17, First Round, Group D |
| 30.07.2016 | | Ross County | – | Cove Rangers | | 7:0 (1:0) |
| Dingwall |
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, Final |
| 13.03.2016 | | Hibernian | – | Ross County | | 1:2 (1:1) |
| Glasgow |
Scottish League Cup 2015/16, Semifinal |
| 31.01.2016 | | Ross County | – | Celtic | | 3:1 (1:1) |
| Glasgow |
Scottish League Cup 2015/16, Quarterfinal |
| 27.10.2015 | | Inverness | – | Ross County | | 1:2 (0:1) |
| Inverness |
Scottish League Cup 2015/16, Third Round |
| 22.09.2015 | | Ross County | – | Falkirk | | 7:0 (3:0) |
| Dingwall |
Scottish League Cup 2015/16, Second Round |
| 25.08.2015 | | Ross County | – | Ayr United | | 2:0 (1:0) |
| Dingwall |
Scottish League Cup 2014/15, Second Round |
| 26.08.2014 | | Stranraer | – | Ross County | | 1:2 (1:1) |
| Stranraer |
Scottish League Cup 2011/12, Second Round |
| 23.08.2011 | | Hamilton Academical | – | Ross County | | 1:2 (1:0) |
| Hamilton |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | Ross County | – | Queen's Park | | 2:1 (0:1) |
| Dingwall |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Ross County | – | Livingston | | 2:1 (1:0) |
| Dingwall |
Scottish League Cup 2009/10, Second Round |
| 25.08.2009 | | Ross County | – | Hamilton Academical | | 2:1 (1:0) |
| Dingwall |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Ross County | – | Montrose | | 5:0 (1:0) |
| Dingwall |
Scottish League Cup 2007/08, First Round |
| 07.08.2007 | | Ross County | – | Elgin City | | 3:1 (1:1) |
| Dingwall |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Ross County | – | Stranraer | | 4:2 (1:0) |
| Dingwall |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | Forfar Athletic | – | Ross County | | 1:4 aet
(0:1, 1:1) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Dumbarton | – | Ross County | | 1:3 (1:2) |
| |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | East Stirlingshire | – | Ross County | | 1:2 (0:0) |
| |
Scottish League Cup 2002/03, Second Round |
| 24.09.2002 | | Ross County | – | Hamilton Academical | | 3:0 (1:0) |
| |
Scottish League Cup 2002/03, First Round |
| 10.09.2002 | | Clyde | – | Ross County | | 0:1 (0:1) |
| |
Scottish League Cup 2001/02, Third Round |
| 09.10.2001 | | Ross County | – | Dundee | | 2:1 |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | Ross County | – | Brechin City | | 3:0 |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | Ross County | – | Albion Rovers | | 1:0 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Ross County | – | Forfar Athletic | | 2:1 aet
(1:1) |
| |
Scottish League Cup 1998, Third Round |
| 19.08.1998 | | Ross County | – | Dundee United | | 2:0 |
| |
Scottish League Cup 1998, Second Round |
| 08.08.1998 | | Greenock Morton | – | Ross County | | 0:1 |
| |
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 1994, First Round |
| 10.08.1994 | | Ross County | – | Queen's Park | | 3:2 |
| |
