Scottish League Cup 2023/24, Group F |
 | 29.07.2023 | | Annan Athletic | – | Raith Rovers | | 2:3 (2:1) |
| Annan |
Scottish League Cup 2023/24, Group F |
| 22.07.2023 | | Annan Athletic | – | Albion Rovers | | 1:2 (1:0) |
| Annan |
Scottish League Cup 2023/24, Group F |
| 18.07.2023 | | Dunfermline Athletic | – | Annan Athletic | | 4:0 (2:0) |
| Dunfermline |
Scottish League Cup 2023/24, Group F |
| 15.07.2023 | | Kilmarnock | – | Annan Athletic | | 3:0 (2:0) |
| Kilmarnock |
Scottish League Cup 2022/23, Second Round |
| 30.08.2022 | | Annan Athletic | – | Aberdeen | | 1:4 aet
(0:0, 1:1) |
| Annan |
Scottish League Cup 2022/23, Group F |
| 19.07.2022 | | Annan Athletic | – | Ayr United | | 1:1 (0:0),
pen. 5:4 |
| Annan |
Scottish League Cup 2022/23, Group F |
| 16.07.2022 | | Annan Athletic | – | Elgin City | | 4:0 (3:0) |
| Annan |
Scottish League Cup 2022/23, Group F |
| 12.07.2022 | | St. Johnstone | – | Annan Athletic | | 0:0,
pen. 4:5 |
| Perth |
Scottish League Cup 2022/23, Group F |
| 09.07.2022 | | Queen of the South | – | Annan Athletic | | 2:3 (1:2) |
| Dumfries |
Scottish League Cup 2021/22, Group F |
| 24.07.2021 | | Motherwell | – | Annan Athletic | | 2:0 (1:0) |
| Motherwell |
Scottish League Cup 2021/22, Group F |
| 20.07.2021 | | Annan Athletic | – | Queen's Park | | 1:2 (1:1) |
| Annan |
Scottish League Cup 2021/22, Group F |
| 13.07.2021 | | Annan Athletic | – | Queen of the South | | 1:3 (0:1) |
| Annan |
Scottish League Cup 2021/22, Group F |
| 10.07.2021 | | Airdrieonians | – | Annan Athletic | | 1:1 (0:0),
pen. 4:5 |
| Airdrie |
Scottish League Cup 2020/21, Group F |
| 10.11.2020 | | Albion Rovers | – | Annan Athletic | | 1:5 (0:4) |
| Coatbridge |
Scottish League Cup 2020/21, Group F |
| 13.10.2020 | | Ayr United | – | Annan Athletic | | 1:0 (1:0) |
| Ayr |
Scottish League Cup 2020/21, Group F |
| 10.10.2020 | | Annan Athletic | – | Stranraer | | 1:1 (0:1),
pen. 4:5 |
| Annan |
Scottish League Cup 2020/21, Group F |
| 06.10.2020 | | Annan Athletic | – | Hamilton Academical | | 3:1 (3:0) |
| Annan |
Scottish League Cup 2019/20, Group E |
| 27.07.2019 | | Motherwell | – | Annan Athletic | | 4:0 (2:0) |
| Motherwell |
Scottish League Cup 2019/20, Group E |
| 23.07.2019 | | Annan Athletic | – | Greenock Morton | | 0:5 (0:3) |
| Annan |
Scottish League Cup 2019/20, Group E |
| 16.07.2019 | | Queen of the South | – | Annan Athletic | | 3:3 (3:1),
pen. 5:4 |
| Dumfries |
Scottish League Cup 2019/20, Group E |
| 13.07.2019 | | Annan Athletic | – | Dumbarton | | 0:1 (0:0) |
| Annan |
Scottish League Cup 2018/19, Group F |
| 24.07.2018 | | Airdrieonians | – | Annan Athletic | | 4:1 (1:0) |
| Airdrie |
Scottish League Cup 2018/19, Group F |
| 21.07.2018 | | Livingston | – | Annan Athletic | | 1:0 (1:0) |
| Linlithgow |
Scottish League Cup 2018/19, Group F |
| 17.07.2018 | | Annan Athletic | – | Berwick Rangers | | 4:0 (2:0) |
| Annan |
Scottish League Cup 2018/19, Group F |
| 14.07.2018 | | Annan Athletic | – | Hamilton Academical | | 1:0 (0:0) |
| Annan |
Scottish League Cup 2017/18, Group E |
| 29.07.2017 | | Annan Athletic | – | Ayr United | | 1:6 (0:4) |
| Annan |
Scottish League Cup 2017/18, Group E |
| 25.07.2017 | | Dumbarton | – | Annan Athletic | | 0:0,
pen. 3:4 |
| Dumbarton |
Scottish League Cup 2017/18, Group E |
| 22.07.2017 | | Annan Athletic | – | Kilmarnock | | 0:2 (0:1) |
| Annan |
Scottish League Cup 2017/18, Group E |
| 15.07.2017 | | Clyde | – | Annan Athletic | | 2:1 (0:0) |
| Cumbernauld |
Scottish League Cup 2016/17, First Round, Group F |
| 30.07.2016 | | East Stirlingshire | – | Annan Athletic | | 0:2 (0:0) |
| Stenhousemuir |
Scottish League Cup 2016/17, First Round, Group F |
| 23.07.2016 | | Annan Athletic | – | Motherwell | | 1:3 (1:1) |
| Annan |
Scottish League Cup 2016/17, First Round, Group F |
| 19.07.2016 | | Rangers | – | Annan Athletic | | 2:0 (1:0) |
| Glasgow |
Scottish League Cup 2016/17, First Round, Group F |
| 16.07.2016 | | Annan Athletic | – | Stranraer | | 1:2 (0:0) |
| Annan |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | Annan Athletic | – | Queen of the South | | 3:4 aet
(0:1, 3:3) |
| Annan |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Dunfermline Athletic | – | Annan Athletic | | 5:1 (2:0) |
| Dunfermline |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Queen of the South | – | Annan Athletic | | 3:0 (0:0) |
| Dumfries |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Hamilton Academical | – | Annan Athletic | | 2:0 (0:0) |
| Hamilton |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | Annan Athletic | – | Dunfermline Athletic | | 1:2 |
| Annan |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Annan Athletic | – | Partick Thistle | | 0:1 (0:0) |
| Annan |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Inverness | – | Annan Athletic | | 4:0 (1:0) |
| Inverness |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Dumbarton | – | Annan Athletic | | 1:1 aet
(0:0),
pen. 5:4 |
| Dumbarton |
Azerbaijan
Armenia
Belarus
Kazakhstan
Moldova
Uzbekistan
Austria
England
Belgium
Bulgaria
Hungary
Germany
FRG
DDR
Netherlands
Georgia
Iceland
Spain
Italy
Latvia
Lithuania
Norway
Poland
Portugal
Serbia
Slovenia
France
Croatia
Montenegro
Czech
Sweden
Scotland
Estonia
Argentina
Brazil
Canada
China
Australia
