Dundee will face one of their Championship promotion rivals in the Betfred Cup group stage.
The Dark Blues were drawn with Inverness Caley Thistle, Raith Rovers, Peterhead and Cove Rangers in Group D of the opening stage of the competition.
And there will be added spice to the contest against the Highlanders after the Dens Park club’s recent approach to speak to Caley boss John Robertson about their vacant manager’s job was denied with a spikey statement from Robertson’s employers.
That promises an awkward meeting between club chiefs John Nelms and Scot Gardiner.
As for their other opponents, there are some Dundee links with former central defensive pair Iain Davidson and Kyle Benedictus expected to still be part of John McGlynn’s Raith squad next season. The Stark’s Park side remained in League One after losing the play-off final to Queen of the South.
League Two champions Peterhead are managed by a man who had two playing spells at Dens Park in Jim McInally.
Cove, meanwhile, are the newest side in the SPFL after thrashing Berwick Rangers in the pyramid play-off.