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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