New manager Tony Docherty was left frustrated as Dundee became the second cinch Premiership club to suffer a Viaplay Cup group-stage exit despite defeating Inverness 1-0 at Dens Park on Sunday.
The Dark Blues – having lost to Airdrie last weekend – knew they needed to beat their Championship opponents by at least a two-goal margin in order to usurp Raith Rovers as one of the four best runners-up and qualify for the last 16.
However, Dundee were unable to find a second goal to add to Zach Robinson’s opener as they joined Tayside rivals St Johnstone in suffering an ignominious first-hurdle exit.
The Dark Blues threatened after five minutes when Mexican striker Diego Pineda shot against the top of the crossbar from close range after Joe Shaughnessy headed a corner back into the danger area.
Inverness went close in the 15th minute when Billy Mckay saw a volley from six yards out tipped over by Jon McCracken before Nathan Shaw curled an effort just beyond the far post after cutting inside Lee Ashcroft.
Mckay and Austin Samuels both missed further opportunities for the Championship side when they got in behind the home defence early in the second half.
Dundee – lifted by the introduction of debutant striker Amadou Bakayoko from the bench at the start of the second half – made the breakthrough on the hour when Zach Robinson’s follow-up header crossed the line before being clawed out by Mark Ridgers after Luke McCowan’s shot had been blocked by the head of Wallace Duffy.
However, the hosts were unable to make their pressure count in the closing stages as recently appointed boss Docherty saw his newly promoted side suffer an early exit from the tournament ahead of their return to the top flight next weekend. The result means Championship side Raith – runners-up in Group F – go through to the last 16.