Late drama has proven to be a feature of Airdrie’s Viaplay Cup campaign, and it was no different at the Caledonian Stadium as Nikolay Todorov put his old club to the sword with an 88th-minute winner.

The Diamonds had little recovery time after Saturday’s bruising encounter with Dundee, and that was reflected in the line-up with Gabby McGill (hamstring) missing out altogether and Rhys McCabe (ankle) only deemed fit enough for a place on the bench. Adam Frizzell recovered significantly from a facial knock to retain his place in midfield.

Josh O’Connor, Dean McMaster, Charlie Telfer and Nikolay Todorov came into the Airdrie side, with Murray Aiken and Calum Gallagher also dropping to the bench.

Although Airdrie started brightly, it was hosts Inverness who had the best of the early chances, Danny Devine heading wide on seven minutes before David Carson sent an ambitious effort wide a minute later.

Airdrie hit back through Todorov, who saw home keeper Cammy Mackay hold his 12th-minute shot at the second attempt.

Midfielder Lewis Nicolson left the field on a stretcher after a lengthy stoppage on 16 minutes, Cameron Harper replacing the unfortunate Inverness man.

Midway through the first half the Diamonds took control of the fixture, and it was an outstanding solo goal from Cammy Ballantyne which opened the scoring.

The defender picked up the ball just inside the Inverness half and drove for goal, evading challenges and teeing himself up for a shot from the edge of the box, which he guided beyond Mackay into the bottom corner.

Airdrie added a second seven minutes later, with Charlie Telfer driving play forward from halfway. Although the move seemed to break down on the edge of the box, the home defence hesitated long enough for Craig Watson to steal possession and pass to Frizzell, who picked out Telfer’s clever run and allowed the midfield man to fire home through Mackay’s legs.

With two assists to his name, Frizzell attempted to get on the scoresheet five minutes from half-time, but his left-footed effort went wide.

A late Inverness free-kick hit the Airdrie wall, and the Diamonds took their two-goal cushion into the break.

The visitors were unlucky not to increase their lead in the opening stages of the second half, O’Connor denied by a timely block after Josh Rae had picked out the speeding forward with a raking pass.

The resultant corner saw a Todorov shot come back off the post, before Aaron Taylor-Sinclair’s follow-up was blocked by a sea of blue shirts.

The home side took heart from their resolute defending, and play began to swing in their favour, Rae reacting well to a miscued effort following a 57th-minute cross.

Billy Mckay found himself in a great position on the hour-mark, but the veteran striker could only fire over from twelve yards out.

The Highlanders did pull one back three minutes later, and it was a stunning finish from Charlie Gilmour, who lashed into the top corner from distance.

Substitute Wallace Duffy nodded over from a 71st-minute corner kick as the hosts pushed for an equaliser, and Frizzell and Gilmour exchanged off-target efforts before a rash challenge handed the hosts a lifeline.

A ball into the corner of the box was met by Mckay, with Ballantyne’s sliding challenge taking man and ball and leaving referee Matthew MacDermid with no option but to point at the spot.

Mckay dusted himself down to take the penalty, sending Rae the wrong way and writing himself into the record books as Inverness’s all-time top scorer.

With the home side in the ascendancy, it looked like the Diamonds would have a battle to hold on for penalties as substitute Austin Samuels curled wide on 86 minutes.

This Airdrie team should never be written off, though, and former Caley Thistle man Todorov showed great composure with just over a minute remaining, controlling Watson’s pass and picking his spot across Mackay to make it 3-2.

As stoppage-time ticked on, the Diamonds had Rae to thank for two outstanding saves, the keeper denying Samuels at point-blank range before somehow getting a big hand to Nathan Shaw’s goalbound effort.

Airdrie now face a trip to bottom side Bonnyrigg Rose on Saturday, although the result may be academic depending on the result of this evening’s match between Dundee and Dumbarton.