The Betfred Cup draw has set up another Tayside derby as Dundee United and St Johnstone were drawn together in Group C.
The Premiership duo – who met on the opening day of the 2020/21 season – will also face Brechin City, Kelty Hearts and Peterhead in the first stage of the tournament.
Meanwhile, James McPake will go head to head with his former club in Group B as Dundee take on Hibs, with the pair joined in their section by Forfar, Brora Rangers and Cove Rangers.
Dunfermline are alongside Kilmarnock, Clyde, Falkirk and Dumbarton in Group E while Raith Rovers take on Inverness Caley Thistle, Cowdenbeath, East Fife and Hearts in Group A.
Raith’s clash with the Jambos promises to be an intriguing encounter in the wake of the capital club’s legal action to halt their relegation to the Championship and, as a result, stop Rovers’ promotion from League One.
The Betfred Cup, which will be shown on Premier Sports, keeps its usual format of eight groups of five teams.
The last 16 is then made up of the eight group winners, four best runners-up and Scotland’s European representatives Celtic, Rangers, Motherwell and Aberdeen.
Group stage games are scheduled for:
Tuesday, October 6
Saturday, October 10
Tuesday, October 13
Tuesday, November 10
Saturday, November 14
North section
Group A
Hearts
Inverness Caledonian Thistle
Cowdenbeath
Raith Rovers
East Fife
Group B
Hibernian
Dundee
Forfar Athletic
Brora Rangers
Cove Rangers
Group C
St Johnstone
Dundee United
Peterhead
Brechin City
Kelty Hearts
Group D
Ross County
Arbroath
Elgin City
Stirling Albion
Montrose
South section
Group E
Kilmarnock
Dunfermline Athletic
Clyde
Dumbarton
Falkirk
Group F
Hamilton Academical
Ayr United
Stranraer
Albion Rovers
Annan Athletic
Group G
St Mirren
Morton
Queen of the South
Partick Thistle
Queen’s Park
Group H
Livingston
Alloa Athletic
Stenhousemuir
Airdrieonians
Edinburgh City