The Betfred Cup draw has thrown up a summer Dundee city derby.
Ray McKinnon and Neil McCann – who both played in the fixture – will manage their teams in it for the first time.
The match will be played in the second half of July. The home side, and the date, has yet to be announced but it is sure to be live on television.
The last time the two sides played was the night Dundee officially relegated their rivals to the Championship.
Another intriguing story of Group C will be ex-Dundee boss Barry Smith coming up against his old side with Raith Rovers.
Cowdenbeath are also in Group C, with Highland League champions Buckie Thistle the other club.
The draw has paired Brechin and Forfar together in Group A and Montrose and Arbroath in Group D.
Dunfermline got a tough draw, with Hearts their first seed. They will also have a Fife derby against East Fife.
Chris Sutton, who helped make the draw, said: “Dundee loved sending Dundee United down so Dundee United will want to put one over on them. It’s a huge game.”
The group winners and four best runners-up progress to the last 16, where they are joined by holders Celtic and fellow European representatives St Johnstone, Aberdeen and Rangers.
The four group games will be played on July 15, July 19, July 22, July 26 and July 29 (subject to broadcast selections). Fixtures will be announced next week.
Full draw –
Group A
ICT
Falkirk
Stirling Albion
Brechin City
Forfar Athletic
Group B
Hearts
Dunfermline
Peterhead
East Fife
Elgin City
Group C
Dundee
Dundee United
Cowdenbeath
Buckie Thistle
Raith Rovers
Group D
Ross County
Hibs
Montrose
Alloa Athletic
Arbroath
Group E
Kilmarnock
Dumbarton
Ayr United
Clyde
Annan Athletic
Group F
Motherwell
Morton
Edinburgh City
Berwick Rangers
Queen’s Park
Group G
Hamilton
QoS
Albion Rovers
Stenhousemuir
East Kilbride
Group H
Partick Thistle
St Mirren
Airdrie
Stranraer
Livingston
