
St Johnstone and St Mirren will both have to play their first-round Co-operative Insurance Cup ties on Ochilview's artificial surface.
Scottish Premier League new boys St Johnstone have been drawn away to Stenhousemuir, who were themselves promoted to Division Two.
St Mirren will face East Stirling, who share Ochilview, on Sunday 2 August.
Shire's Third Division rivals Annan face the longest journey to play Inverness, relegated from the SPL.
The SPL sides have been pulled into the first round of matches because Scotland has six teams in European competition and two sides were required to make up the numbers.
Newly promoted St Johnstone and St Mirren, who only escaped relegation on goal difference, were the lowest placed of the top-tier teams and therefore had to enter the Co-operative Insurance Cup at the earliest stage.
Second Division East Fife host Raith Rovers, who won promotion to Division One, in a Fife derby.
Co-operative Insurance Cup first-round draw
Brechin City v Elgin City
Queen's Park v Queen of the South
Inverness Caledonian Thistle v Annan Athletic
Stenhousemuir v St Johnstone
Ross County v Montrose
East Stirlingshire v St Mirren
Partick Thistle v Berwick Rangers
East Fife v Raith Rovers
Dundee v Stranraer
Stirling Albion v Ayr United
Airdrie United v Alloa Athletic
Cowdenbeath v Morton
Peterhead v Arbroath
Albion Rovers v Livingston
Clyde v Forfar Athletic
Dumbarton v Dunfermline Athletic
Ties to be played on the following dates
First round - Saturday 1 or Sunday 2 August 2009
Second round - Tuesday 25 or Wednesday 26 August 2009
Third round - Tuesday 22 or Wednesday 23 September 2009
Fourth round - Tuesday 27 or Wednesday 28 October 2009
Semi-finals - Tuesday 2 or Wednesday 3 February 2010
Final - Sunday 21 March 2010
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