Terry Butcher's side were third in the table, just a point behind Aberdeen on the back of a hugely positive start to the season. Hearts, in contrast, had taken just a solitary point from their previous seven league matches and were beginning to look rather leg weary. It would surely be no contest.
Three months on, however, and the landscape has changed. The scales have shifted to the point where Inverness will no longer be the overwhelming favourites when the teams meet in the last four of the competition for a second season in a row at Easter Road on Sunday.
Hearts are still somewhat bedraggled and virtually resigned to Championship football next season but a battling draw and a win in their last two matches has given them a timely tonic. The biggest change, however, has come in the fortunes of Inverness. Butcher has departed for Hibernian and the head of steam that had been built up has evaporated under his replacement John Hughes.
From a team with a more than reasonable chance of finishing as best-of-the-rest behind Celtic, Inverness' season has nose-dived. Should Dundee United defeat St Johnstone this evening, they will bump Hughes' side down to fifth place in the table.
The new manager did not seem unduly worried following his side's latest setback - a 2-0 defeat by Kilmarnock courtesy of goals from Lee Ashcroft and Kris Boyd - but this was a surprisingly lacklustre performance from a group of players who had seemed so vibrant under Butcher just a few short months ago.
Most worrying for Inverness is the fact that the goals have dried up for Billy McKay. The 25 year-old with the remarkable scoring record in recent seasons has shown himself to be merely mortal of late, notching just once in his past six games. He received little service on Saturday but was uncharacteristically wasteful with the two good opportunities that came his way, heading a first-half chance wide of goal before his shot early in the second was well saved by Craig Samson.
Assuming he is not sold before the transfer deadline on Friday, Inverness will lean heavily on McKay to provide the goals to take them past Hearts and into the League Cup final. It is a responsibility he will not shirk.
"If I miss a chance I just put it out my head right away," said the striker hoping to reach his first senior cup final. "When the next one comes to me I'm confident I can put it away. I missed a couple [on Saturday] but I'm confident if the ball comes to me in the box I'll put it away next week. You've got to be optimistic. If we win we're in the final so we'll be doing everything possible to do that."
Kilmarnock, League Cup winners two years ago, have no such cup aspirations this season, the focus solely on trying to achieve as high a league placing as possible. After a difficult start, Allan Johnston seems to have achieved an ideal fusion of experience and youth in his selection, the Kilmarnock manager giving a first career start to 17-year-old Greg Kiltie on Saturday alongside old heads such as Boyd, Samson and Manuel Pascali.
It may get better yet for Kiltie should Johnston succeed in bringing Alexei Eremenko back to the club. The Finn, who spent a successful season on loan in Ayrshire three years ago, was on the Rugby Park pitch on Saturday to conduct the half-time draw before sitting down for contract talks over the weekend with Michael Johnston, the Kilmarnock chairman.
As a former season ticket holder, Kiltie was among many Kilmarnock fans mesmerised by Eremenko and hopes now to get the chance to play alongside his one-time hero.
"Eremenko was brilliant when I watched him here a few years ago and I'd love if it if he came back so I could learn off him," he said." I had a season ticket when he was here and he was always doing Cruyff turns and switching play - he was brilliant to watch. If he can come back and do that again it would be amazing.
"At the time watching in the stand I couldn't have thought that one day I could be playing alongside him. That would be a dream come true."