The Scottish League Cup draw has pitted Hearts against Inverness Caledonian Thistle in the northern Group C.
Hearts did not get past the group stage last year finishing third overall in a group with Dunfermline, Peterhead, East Fife and Elgin City.
The runners-up of each group in the northern and southern section go into a “best-runners up group” with the top four progressing into the next stage.
Hearts and Inverness are no strangers to one another but the latter have not defeated Craig Levein’s side in a match since 2015. Raith Rovers, Cowdenbeath and Scottish Highland League champions Cove Rangers complete their group.
2016 League Cup winners Ross County, who were relegated from the Scottish Premiership this season, will face another Scottish Championship outfit in Dundee United as well as Arbroath, Elgin City and Alloa in Group A.
St Johnstone, who finished outside the top six in the Premiership for the first time in six seasons, will take on Falkirk, Montrose, East Fife and Forfar in Group B.
Rounding off the northern section in Group D is Dundee, Dunfermilne, Stirling Albion, Brechin and Peterhead.
In the southern groups, the top seed of Group E Partick Thistle, who lost to Livingstone 3-1 on aggregate in the Premiership play-off, will face Morton, Albion Rovers, Ayr and Stenhousemuir.
Hamilton will take on the newly promoted Livingstone in Group F along with Berwick Rangers, Airdrieonians and Annan Athletic,
In Group G Motherwell face Queen of the South, Clyde, Edinburgh City, who are yet to win a game in the cup, and Stranraer.
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In the final group, Group H, Steve Clarke’s Kilmarnock take on Queens Park, who Liverpool’s Andy Robertson played for in the 2012/13 season.
St Mirren, Dunbarton and Spartans, who are in the League Cup for the first time, complete their group.
The top four seeds of Celtic, Aberdeen, Rangers and Hibs, enter the competition in the second round. They all receive a bye for the group stage due to being in the European competitions.