The journey to Hampden for the League Cup begins on 5 August
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Scottish Football League newcomers Annan Athletic have been drawn away to Dumbarton in the first round of the Co-operative Insurance Cup.
First Division favourites St Johnstone travel to Stenhousemuir, while Peterhead host Dunfermline Athletic.
Ross County entertain Airdrie United in a clash of the newly-promoted clubs to the First Division.
Partick Thistle welcome Forfar, Morton go to Stranraer and Clyde host Second Division Queen's Park.
First Division clubs Dundee and Queen of the South received byes into the second round.
Rangers are the trophy holders, having beaten Dundee United in a penalty shoot-out after a thrilling 2-2 draw at Hampden in March.
Co-operative Insurance Cup - first round draw:
Montrose v Cowdenbeath Ross County v Airdrie United Dumbarton v Annan Athletic Peterhead v Dunfermline Stranraer v Morton Alloa Athletic v Elgin City Clyde v Queen's Park Albion Rovers v Raith Rovers Ayr United v Berwick Rangers East Fife v Brechin City Arbroath v Stirling Albion Partick Thistle v Forfar Athletic East Stirlingshire v Livingston Stenhousemuir v St Johnstone
Ties to be played on 5 & 6 August.
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