Scottish League Cup 2023/24, Quarterfinals |
| 27.09.2023 | | Ross County | | Aberdeen | | 1:2 (0:1) |
| Dingwall |
Scottish League Cup 2022/23, Second Round |
| 31.08.2022 | | Ross County | | Celtic | | 1:4 (0:2) |
| Dingwall |
Scottish League Cup 2021/22, Group C |
| 18.07.2021 | | Ross County | | Dundee | | 0:3 |
| Dingwall |
Scottish League Cup 2021/22, Group C |
| 10.07.2021 | | Forfar Athletic | | Ross County | | 3:0 |
| Forfar |
Scottish League Cup 2020/21, Quarterfinal |
| 16.12.2020 | | Livingston | | Ross County | | 2:0 (2:0) |
| Livingston |
Scottish League Cup 2019/20, Second round |
| 17.08.2019 | | Partick Thistle | | Ross County | | 3:2 aet (0:0, 1:1) |
| Glasgow |
Scottish League Cup 2018/19, Second round |
| 19.08.2018 | | Hibernian | | Ross County | | 3:2 (1:1) |
| Edinburgh |
Scottish League Cup 2018/19, Group A |
| 25.07.2018 | | Arbroath | | Ross County | | 4:1 (1:1) |
| Arbroath |
Scottish League Cup 2017/18, Second round |
| 09.08.2017 | | Ross County | | Motherwell | | 2:3 aet (0:0, 1:1) |
| Dingwall |
Scottish League Cup 2016/17, First Round, Group D |
| 26.07.2016 | | Alloa Athletic | | Ross County | | 3:2 (2:2) |
| Alloa |
Scottish League Cup 2014/15, Third Round |
| 23.09.2014 | | Ross County | | Hibernian | | 0:2 (0:2) |
| Dingwall |
Scottish League Cup 2013/14, Second Round |
| 27.08.2013 | | Stranraer | | Ross County | | 3:2 (0:1) |
| Stranraer |
Scottish League Cup 2012/13, Second Round |
| 28.08.2012 | | Ross County | | Raith Rovers | | 1:4 (0:2) |
| Dingwall |
Scottish League Cup 2011/12, Third Round |
| 21.09.2011 | | Ross County | | Celtic | | 0:2 (0:1) |
| Dingwall |
Scottish League Cup 2010/11, Third Round |
| 22.09.2010 | | Ross County | | Dundee United | | 1:2 aet (0:0, 1:1) |
| Dingwall |
Scottish League Cup 2009/10, Third Round |
| 22.09.2009 | | Ross County | | Dundee United | | 0:2 (0:1) |
| Dingwall |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Ross County | | Airdrie United | | 2:3 aet (1:1, 2:2) |
| Dingwall |
Scottish League Cup 2007/08, Second Round |
| 29.08.2007 | | Dundee United | | Ross County | | 2:1 (0:0) |
| Dundee |
Scottish League Cup 2006/07, Second Round |
| 22.08.2006 | | Alloa Athletic | | Ross County | | 2:1 (1:0) |
| Alloa |
Scottish League Cup 2005/06, Second Round |
| 23.08.2005 | | Ross County | | Ayr United | | 1:2 (1:2) |
| |
Scottish League Cup 2004/05, Second Round |
| 24.08.2004 | | Ross County | | Inverness | | 0:1 (0:0) |
| |
Scottish League Cup 2003/04, Second Round |
| 23.09.2003 | | Ross County | | Queen of the South | | 0:3 (0:2) |
| |
Scottish League Cup 2002/03, Third Round |
| 23.10.2002 | | Hearts | | Ross County | | 3:0 (0:0) |
| Edinburgh |
Scottish League Cup 2001/02, Quarterfinal |
| 28.11.2001 | | Ross County | | Rangers | | 1:2 |
| |
Scottish League Cup 2000/01, Second Round |
| 22.08.2000 | | Ross County | | St. Mirren | | 1:3 aet (1:1) |
| |
Scottish League Cup 1999/00, Second Round |
| 18.08.1999 | | Dundee United | | Ross County | | 3:1 aet (1:1) |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | Ross County | | Falkirk | | 0:3 |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | Queen's Park | | Ross County | | 3:1 aet |
| |
Scottish League Cup 1995, First Round |
| 05.08.1995 | | Ross County | | Arbroath | | 0:2 |
| |
Scottish League Cup 1994, Second Round |
| 17.08.1994 | | Ross County | | Raith Rovers | | 0:5 |
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