Robertson, Hearts’ record league goalscorer, is in his second spell in charge of the Highland club and will bring his team to Gorgie for the group fixture.
The Betfred Cup was to prove the ultimate undoing of Ian Cathro as Hearts manager last year and the club will be looking to start next season’s competition in more positive fashion.
They will also have to contend with Raith Rovers, Cowdenbeath and Highland League winners Cove Rangers, as well as Caley Thistle, in Group C.
Having failed to negotiate the group stage last term, despite their status as one of the top seeds, Cathro was sacked. It meant the capital side started the league season without a manager and on the back foot.
Craig Levein was eventually appointed as Cathro’s replacement and will start his first full season of his second stint at the helm this summer
The group stage of the contest will see 40 clubs playing four games each, with the eight group winners and four best runners up all progressing to the last 16, where they will be joined by holders Celtic and their fellow European representatives – Aberdeen, Rangers and Hibernian.
The draw for the initial phase of the contest, which will kick off on 14 July, has pitted former colleagues Levein and Robertson against each other, while the Hearts boss will also have to out-manoeuvre Raith Rovers and Cowdenbeath, his first professional club, as player and as boss.
The Central Park side will also face a juicy tussle with Cove Rangers, who will be seeking revenge after the Fife side edged past them in the recent controversial League 2 play-off final.
That game ended in a mass brawl, as the Aberdeen side raged against a contentious winning goal, and Cove finished the game with eight men, while Cove manager John Sheran and his Cowdenbeath counterpart Gary Bollan were both sent to the stands.
The dates and venues for all of the fixtures will be announced next week, along with which games have been scheduled for television.
While Hearts will fancy their chances of progressing this time around, the other top seeds are also likely to be content with their groupings.
This year’s Betfred and Scottish Cup finalists Motherwell have been drawn in Group G against Queen of the South, Clyde and Stranraer and it will be the second year in a row that they have also been pitted against League Two side Edinburgh City.
With two home and two away fixtures each, in a bid to increase the competitiveness and excitement, all matches that end in a draw will go straight to penalties, with the shoot-out winners earning a single bonus point.
Kilmarnock were the highest finishing team in this season’s Premiership in the draw, and will face Dumbarton, Queens Park and Lowland League champions Spartans in Group H – they also have the tricky task of bettering Championship winners St Mirren.
Killie manager Steve Clarke’s former club, the Paisley outfit will have a new man at the helm following manager of the year Jack Ross’ departure to Sunderland and his successor will be keen to prove they can maintain the form that earned them promotion with a strong start in the first domestic cup competition of the new season.
Fellow newcomers to the top tier, Livingston, who are battling to keep hold of their own manager, David Hopkin, are second seeds in Group F and will have to better Hamilton, Berwick Rangers, Annan Athletic and Airdrie if they are to ensure progress to the next phase.
Relegated Partick Thistle will hope to begin their redemption process by bossing Group E. But they will face a difficult challenge against Morton, League One champions Ayr United, Albion Rovers and Stenhousemuir.
Ross County and Dundee United, both likely to be Championship promotion contenders, are drawn together in Group A, while in Group B Falkirk are the likeliest challengers to St Johnstone for top spot.
It is a similar story for Dunfermline in Group D, where they will have a fight for superiority with their former coach Neil McCann and his top-flight Dundee side.
BETFRED LEAGUE CUP GROUP STAGE DRAW
Queen of the South