Motherwell will take on local rivals Airdrie for the first time in 14 years after being paired together in the group-stage draw for the Premier Sports Cup.
The Lanarkshire foes have not met since a Scottish Cup tie back in 2007.
Last year's League Cup runners up Livingston will face Raith Rovers, Alloa, Cowdenbeath and Brechin in Group D, while Championship winners Hearts face four tricky ties against northern opposition after ending up in Group A alongside Inverness, Peterhead, Stirling and Cove Rangers.
Kilmarnock are still reeling after being relegated from the Premiership earlier this week but there is some positive news in that they have landed a favourable draw in Group G, with Greenock Morton, Clyde, Stranraer and East Kilbride for opposition.
Last season's competition winners St Johnstone – who made it a double after adding the Scottish Cup to last season's incredible haul – have been handed a bye to the second round along with Steven Gerrard's new Scottish champions Rangers and fellow European entrants Celtic, Hibernian and Aberdeen.
Games will take place over five rounds of matches spread between July 10 and July 25. The final list of fixtures is still to be confirmed.
Premier Sports Cup group stage draw:
Group A – Hearts, Inverness, Peterhead, Cove Rangers, Stirling Albion.
Group B – Dundee Utd, Arbroath, East Fife, Elgin, Kelty Hearts.
Group C – Ross County, Dundee, Forfar, Montrose, Brora Rangers.
Group D – Livingston, Raith Rovers, Alloa, Cowdenbeath, Brechin.
Group E – Hamilton, Ayr United, Falkirk, Albion Rovers, Edinburgh City.
Group F – Motherwell, Queen of the South, Airdrie, Annan, Queen's Park.
Group G – Kilmarnock, Greenock Morton, Clyde, Stranraer, East Kilbride.
Group H – St Mirren, Dunfermline, Stenhousemuir, Partick Thistle, Dumbarton.