Season Round date Home Result Guest
2010/2011 Round of 16 21/09/2010 Rangers FC Rangers FC 7:2 Dunfermline Athletic Dunfermline Athletic
2009/2010 1. Round 02/08/2009 East Stirlingshire FC East Stirlingshire FC 3:6 St. Mirren FC St. Mirren FC
2008/2009 1. Round 05/08/2008 Stranraer FC Stranraer FC 3:6 Greenock Morton FC Greenock Morton FC
2023/2024 Group D 19/07/2023 Edinburgh City Edinburgh City 3:5 Kelty Hearts Kelty Hearts
2020/2021 Group C 07/10/2020 Brechin City FC Brechin City FC 2:6 Dundee United Dundee United
2019/2020 Round of 16 17/08/2019 Hibernian FC Hibernian FC 5:3 aet Greenock Morton FC Greenock Morton FC
2018/2019 Group D 25/07/2018 Brechin City FC Brechin City FC 1:7 Dunfermline Athletic Dunfermline Athletic
2018/2019 Group G 14/07/2018 Queen Of The South Queen Of The South 5:3 Stranraer FC Stranraer FC
2017/2018 Group G 25/07/2017 Albion Rovers Albion Rovers 4:4 Hamilton Academical Hamilton Academical
2016/2017 Group A 23/07/2016 Dundee FC Dundee FC 6:2 Dumbarton FC Dumbarton FC
2013/2014 Round of 16 24/09/2013 Hibernian FC Hibernian FC 5:3 Stranraer FC Stranraer FC
2013/2014 1. Round 03/08/2013 East Fife FC East Fife FC 2:6 aet Greenock Morton FC Greenock Morton FC
2012/2013 1. Round 04/08/2012 Stranraer FC Stranraer FC 0:8 Livingston FC Livingston FC
2010/2011 2. Round 25/08/2010 Kilmarnock FC Kilmarnock FC 6:2 Airdrie United FC Airdrie United FC
2010/2011 1. Round 31/07/2010 Stranraer FC Stranraer FC 1:7 Greenock Morton FC Greenock Morton FC
2023/2024 Round of 16 19/08/2023 Airdrieonians FC Airdrieonians FC 3:4 aet Ross County FC Ross County FC
2023/2024 Group C 18/07/2023 Cove Rangers Cove Rangers 5:2 Clyde FC Clyde FC
2022/2023 Group C 23/07/2022 Ross County FC Ross County FC 7:0 East Fife FC East Fife FC
2022/2023 Group H 12/07/2022 Hamilton Academical Hamilton Academical 5:2 Stranraer FC Stranraer FC
2022/2023 Group H 09/07/2022 Stranraer FC Stranraer FC 2:5 Queen's Park FC Queen's Park FC
2021/2022 Group C 24/07/2021 Dundee FC Dundee FC 5:2 Forfar Athletic Forfar Athletic
2021/2022 Group B 14/07/2021 Dundee United Dundee United 6:1 Elgin City Elgin City
2020/2021 Group C 10/10/2020 St. Johnstone FC St. Johnstone FC 7:0 Brechin City FC Brechin City FC
2020/2021 Group F 06/10/2020 Albion Rovers Albion Rovers 2:5 Ayr United Ayr United
2019/2020 Semi-finals 02/11/2019 Hibernian FC Hibernian FC 2:5 Celtic FC Celtic FC
2019/2020 Group C 17/07/2019 Stirling Albion FC Stirling Albion FC 1:6 Arbroath FC Arbroath FC
2019/2020 Group E 16/07/2019 Greenock Morton FC Greenock Morton FC 6:1 Dumbarton FC Dumbarton FC
2019/2020 Group G 13/07/2019 Berwick Rangers Berwick Rangers 0:7 Ayr United Ayr United
2018/2019 Group C 17/07/2018 Cowdenbeath FC Cowdenbeath FC 2:5 Inverness CT Inverness CT
2017/2018 Group E 29/07/2017 Annan Athletic Annan Athletic 1:6 Ayr United Ayr United
2017/2018 Group C 25/07/2017 Buckie Thistle Buckie Thistle 1:6 Raith Rovers Raith Rovers
2017/2018 Group D 25/07/2017 Hibernian FC Hibernian FC 6:1 Arbroath FC Arbroath FC
2017/2018 Group G 22/07/2017 East Kilbride FC East Kilbride FC 2:5 Albion Rovers Albion Rovers
2016/2017 Group C 30/07/2016 Inverness CT Inverness CT 7:0 Arbroath FC Arbroath FC
2016/2017 Group D 30/07/2016 Ross County FC Ross County FC 7:0 Cove Rangers Cove Rangers
2016/2017 Group A 30/07/2016 Dundee FC Dundee FC 7:0 Forfar Athletic Forfar Athletic
2016/2017 Group C 19/07/2016 Dundee United Dundee United 6:1 Cowdenbeath FC Cowdenbeath FC
2015/2016 Round of 16 22/09/2015 Ross County FC Ross County FC 7:0 Falkirk FC Falkirk FC
2015/2016 1. Round 01/08/2015 Annan Athletic Annan Athletic 3:4 aet Queen Of The South Queen Of The South
2013/2014 1. Round 03/08/2013 Stranraer FC Stranraer FC 4:3 Brechin City FC Brechin City FC
2013/2014 1. Round 03/08/2013 Airdrieonians FC Airdrieonians FC 4:3 Stenhousemuir FC Stenhousemuir FC
2012/2013 1. Round 04/08/2012 Ayr United Ayr United 6:1 Clyde FC Clyde FC
2012/2013 1. Round 04/08/2012 Queen Of The South Queen Of The South 5:2 Alloa Athletic Alloa Athletic
2012/2013 1. Round 04/08/2012 Raith Rovers Raith Rovers 4:3 Berwick Rangers Berwick Rangers
2011/2012 2. Round 23/08/2011 Greenock Morton FC Greenock Morton FC 3:4 St. Mirren FC St. Mirren FC
2010/2011 Round of 16 21/09/2010 Falkirk FC Falkirk FC 4:3 Heart of Midlothian Heart of Midlothian
2010/2011 1. Round 31/07/2010 Dunfermline Athletic Dunfermline Athletic 5:2 Arbroath FC Arbroath FC
2008/2009 2. Round 26/08/2008 Hibernian FC Hibernian FC 3:4 aet Greenock Morton FC Greenock Morton FC
2008/2009 2. Round 26/08/2008 St. Mirren FC St. Mirren FC 7:0 Dumbarton FC Dumbarton FC
2008/2009 1. Round 05/08/2008 Partick Thistle Partick Thistle 4:3 aet Forfar Athletic Forfar Athletic
League Cup
League Cup

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