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 |
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