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.
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
Inverness Caledonian Thistle
Queen of the South