Caley Thistle progressed into the next stage of the Premier Sports Cup – after winning 5-3 on penalties against Cove Rangers following a 1-1 draw.
The bonus-point win takes Inverness on to 11 points, which earns them a second round berth.
Three wins prior to this closing group stage showdown had the Highlanders on the cusp of progressing for the first time in six years.
Roddy MacGregor put Inverness in front early on, but Mitch Megginson struck back soon after, and there was to be no regulation time clincher.
Aberdeen-based Cove joined Inverness in the Championship after winning League 1 last term under Paul Hartley.
Gearing up for Championship starts
They get their second-tier campaign started under new boss Jim McIntyre next Saturday when Raith Rovers come their way, while ICT host another promoted side in Owen Coyle’s Queen’s Park.
This was the fourth such recent League Cup meeting between these north opponents, with ICT leading 2-1 in the head-to-heads.
However, that Cove win came last season when they deservedly ran out 3-1 victors, so home head coach Billy Dodds knew the dangers.
A 3-2 defeat by Kelty Hearts on Tuesday contributed to Cove bowing out of the competition, while ICT were out to win Group F and secure a seeded spot in the last 16.
Six-year wait for ICT progression
The last time the club made it through to the second stage was in 2016 when Alloa then knocked them out.
Remarkable risers Cove, who have only been in the League Cup for four seasons, have yet to get past the groups.
Caley Thistle went into this closing cup-tie on the back of a fine 4-0 win against League 2 Albion Rovers.
Dodds brought Mark Ridgers, Nathan Shaw, Zak Delaney and George Oakley into the starting 11, with Cammy MacKay, Aaron Doran, Austin Samuels and Billy Mckay all subs.
McIntyre, who was without injured midfielders Blair Yule and Jamie Masson, made two changes to the team which slipped up against Kelty.
In came Scott Ross and Robbie Leitch for Morgyn Neill and Gerry McDonagh, who were on the bench.
MacGregor and Megginson hit mark
The deadlock was broken on 13 minutes when Nathan Shaw flipped the ball into the box and MacGregor diverted a header past Kyle Gourlay. With Livi in front in their game, this was a welcome lead for the hosts.
However, it was all-square just six minutes later when Fyvie’s corner from the right was not cleared with conviction and Megginson lashed home the leveller from 12 yards.
Gourlay had to be alert to keep out a drive from MacGregor after a slip-up let him in as Caley Thistle sought a second goal.
The Cove keeper then pushed clear an Oakley shot after the forward latched on to a pass from Robbie Deas.
It was level-pegging at the break, which seemed a fair outcome from the opening 45 minutes.
Challenges flying in all over the pitch
The early stages of the second half were fiery, with Cove’s Fraser Fyvie and Scott Ross booked for fouls and others walking tightropes.
Former ICT and Ross County ace Iain Vigurs was a fraction away from putting Cove ahead, but he nodded over the bar from inside the six-yard box after Reynolds headed it goalwards.
Caley Jags striker Billy Mckay, who replaced Oakley, was not far off the mark with a low drive on 65 minutes when he was sent clear by Doran, but his effort skidded just past the right post.
Sub Steven Boyd let fly with a long-ranger as the clock ticked down, but Gourlay got down smartly to push it wide.
Cove’s final chance came when Megginson’s shot was blocked just in time by Deas.
There was to be no winner and spot-kicks were the route to decide the bonus point.
Spot-kick drama for ICT bonus point
Boyd, Samuels, Harper, Billy Mckay put away their penalties, while Megginson, Leitch and Shay Logan kept Cove in it.
A tame effort from Fyvie was saved by Ridgers and midfielder Scott Allardice slotted away his for a 5-3 outcome.
CALEY THISTLE (4-2-3-1) – Ridgers 6, Duffy 6 (Doran 73), Harper 6, Deas 6, Carson 7, MacGregor 6, Oakley 6 (Billy Mckay 67), Daniel MacKay 6 (Samuels 67), Allardice 6, Shaw 6 (Boyd 78), Delaney 6. Subs not used – MacKay (GK), Hyde, Cairns, Nicolson.
COVE RANGERS (4-1-4-1) – Gourlay 7, Logan 6, Towler 6, Scully 6, Ross 6, Megginson 6, McIntosh 6 (McDonagh 78), Vigurs 6, Leitch 6, Fyvie 6, Reynolds 6. Subs not used – McKenzie (GK), Neill, McAllister, Thomas.
Referee – Alan Newlands.
Attendance – 1020.
Man of the match – Kyle Gourlay.
Conversation