Inverness reached the League Cup semi-final last season, only to lose out in a penalty shootout to Hearts at Easter Road.
And manager Terry Butcher was hoping the disappointment of going so close last season would spur his players on to go one better this time around after their excellent start to the Scottish Premiership campaign. However before Caley Thistle could start thinking about cup final days out, a tricky tie away to Championship side Dundee at a drizzly Dens Park had to be overcome.
An early goal after only 10 minutes from Billy McKay – his seventh of an already impressive season for the Northern Ireland international – settled any nerves with the forward latching on to captain Richie Foran’s scuffed shot to steer the ball beyond Kyle Letheren in the Dundee goal.
McKay almost scored a second three minutes after the break, but his overhead kick bounced off the crossbar.
Dundee grew in confidence after that let-off.
The second half proved to be a nervy watch for the small band of Caley Thistle supporters among the 1,682-strong crowd who had travelled to Dens Park for the match.
However Caley Thistle goalkeeper Dean Brill was in inspired form, making several key saves to ensure his team progressed.