Troubled League One side Caley Thistle held Championship hosts Livingston 2-2 in the SPFL Trust Trophy – before being edged out on penalties.
Duncan Ferguson’s team, with administration on the cards should suitable investment not be found by Wednesday night, have plenty of hurdles to face.
This fourth round Challenge Cup tie, earned by beating League Two Stirling Albion 3-0, was always going to be a testing tie, but they were a real match here.
Inverness are ninth in their division with just one win so far since their relegation from the Championship this year.
The Livi Lions, who dropped down from the Premiership in May, are third in the second-tier and should be in title contention with Falkirk and Ayr United in 2025.
A hamstring injury meant ICT were without on-loan Dundee forward Charlie Reilly, who made his debut in last week’s 1-0 league loss at Arbroath.
Defender Wallace Duffy and midfielder Keith Bray were handed starts, while goalkeeper Jack Newman was in the line-up for the first time since August 10.
With heavy rain, sleet and a dash of thunder thrown in, it was miserable before kick-off.
Caley Thistle strike first blow in tie
After soaking up early pressure, Inverness struck first blow when Paul Allan scored his first goal for the club by glancing home a header from a pin-point cross from Luis Longstaff on 10 minutes.
However, the lead lasted a mere seven minutes as ex-St Johnstone and Aberdeen forward Stevie May, whose shot from a Scott Pittman assist, flew in off the post, offering no chance to Newman.
The Lions were in front on 28 minutes when a long ball over the top saw May get the better of Wallace Duffy and his cross was nodded home by Pittman.
Inverness responded in ideal fashion two minutes later as Charlie Gilmour tapped the ball into the net after Adam Mackinnon’s corner was knocked into the danger zone by Bray.
ICT skipper Billy Mckay then watched his lob tipped over by Marcelo Pitaluga after being lined up by Allan.
Shoot-out earned by strong display
Adam Mackinnon almost put ICT ahead again in the second half, but two fine Pitaluga stops kept him out before Longstaff’s follow-up was cleared off the line by Ryan McGowan.
Inverness remained a threat and Mackinnon was unlucky to put too much height on his finish when he met a cross from Bray as they sought another goal.
Livi were the stronger side in the closing stages, but it was down to spot-kicks to settle it.
After four finished penalties apiece, Robbie Thompson’s strike was saved by Pitaluga and Stephen Kelly stroked away the clincher for a 5-4 scoreline.
Different scene-setter ahead of clash
Inverness were on a six game unbeaten streak against the Lions, winning the last four encounters, including two cup victories here in West Lothian two seasons ago under Billy Dodds in Premiership v Championship contests.
Although there is still one level between these sides, Livi have begun their season in strong fashion, without losing a league game and firmly expected to be in the title shake-up.
ICT’s off-field troubles are not bettered by results on it, but this was a free hit.
It was a chance to start building momentum, with the home game in League One against Annan next week vital, especially should they get a 15-point punishment by entering administration.
Caley Thistle played with a freedom
Like the first half at Arbroath last week, Caley Thistle didn’t show there was any weight on their shoulders.
They attacked the Lions when they could, asked questions, won free-kicks and for a low-scoring team, took their chances here.
It is very much like the players wearing the ICT jersey feel a sense of freedom when they can get on to the park with a chance to change the narrative, if even for a little while.
Ferguson last week spoke about how the players will be watched by potential future clubs should their Inverness careers be ended by administrators. Many will be catching the eye.
Scoring midfielders boost Inverness
With just six goals netted in their opening nine League One fixtures, and six draws within that cycle, it’s clear a clinical edge has been missing for Inverness.
Therefore, Ferguson will be heartened to see two midfielders arrive in the box and crash home goals against their higher-level opponents.
Whatever happens in terms of administration, the team – in whatever form, will need results to improve their chances of League One progress – or survival.
Ferguson proud of his gutsy players
At full-time, Ferguson, who says he hopes his still in charge next week, said: “We were a bit unlucky with the penalties. We don’t seem to get a break.
“I fancied us when we went to penalties. I felt we rode our luck in the second half when they pushed on at us, although we defended well. We also had two or three chances, but could not get a third goal.
“I thought it was a very good first half performance. They came into it strongly in the second half and we defended well enough.
“Had we reached the quarter-finals, it would be a fantastic lift for the club. It would also have given us a few quid (£30,000 instead of £20,000).
“Livingston had conceded just three goals in nine Championship games before today. All credit to the players to come away with a 2-2 draw. We’re galvanised and showed great fighting spirit. The players did this club proud.”
Midweek deadline for club chiefs
And Ferguson explained all eyes are on the midweek verdict from the boardroom.
He added: “People have told me it’s Armageddon on Wednesday. It seems after Wednesday, it’s not looking good.
“I believe this team is good enough to be promoted out of League One, but if we go into administration, most of the players will probably go and we will be left with a young squad. The staff will probably go, as will I. We will see.”
LIVINGSTON (4-3-3): Pitaluga, Clarke (Yengi 85), Nottingam, McGowan, Brandon, Kelly, Finlayson, Pittman, May (Winter 72), Lawal (Montana 72), Smith (Sole 55).
Subs not used: Prior (GK), McAlear, Green, Muirhead, Stark.
CALEY THISTLE (4-5-1): Dibaga, Nolan (Strachan 62), Savage, Duffy, Davidson, Longstaff, Allan (MacLeod 62), Mackinnon, Gilmour, Bray (Thompson 84), Mckay.
Subs not used: Dibaga (GK), Brooks, Mackay, Ferguson, Ewan.
Referee: Colin Steven.
Man of the match: Stevie May.
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