Former Caley Thistle striker Nikolay Todorov scored an 89th minute winner as Airdrieonians won 3-2 at the Caledonian Stadium.
Caley Thistle had battled back after being 2-0 down at the break, as Cameron Ballantyne and Charlie Telfer had the Diamonds ahead the break.
Charlie Gilmour’s stunning strike and Billy Mckay’s penalty drew Caley Thistle level in the second-half however Todorov’s late goal earned Airdrieonians the win.
Billy Dodds made five changes to the side which was beaten last Tuesday by Dumbarton as Cameron Mackay, Zak Delaney, Lewis Nicolson, Aaron Doran and, new signing Luis Longstaff came into the side. Mark Ridgers, Wallace Duffy, Cameron Harper and Austin Samuels dropped to the bench while Sean Welsh missed out after coming off injured against Dumbarton.
Caley Thistle had the first chance of the match as Nathan Shaw’s corner found the head of Danny Devine in the box but his header was wayward.
Airdrie threatened early on as Todorov saw an early effort gathered by Cameron Mackay at the second attempt.
Lewis Nicolson was forced off on a stretcher with a nasty looking knee injury and was replaced by Cameron Harper after 15 minutes on the clock.
The visitors then had the breakthrough after Jake Davidson lost the ball and Cameron Ballantyne collected in and broke forward and saw his shot from the edge of the box go low and hard past Cameron MacKay after 22 minutes.
The visitors doubled their lead after 29 minutes, Danny Devine was robbed in the box and Adam Frizzell was able to put Charlie Telfer through on goal and he finished past Cameron MacKay to make it 2-0.
Caley Thistle pressed for a way back into the game and Billy Dodds made three changes at the half-time break as Wallace Duffy, Adam Brooks and Keith Bray replaced Danny Devine, Jake Davidson and Aaron Doran.
Airdire were close to a third just after the break as a swung in corner found Nikolay Todorov in the box but his effort hit the post as Caley Thistle got the ball clear.
Caley Thistle pressed to get back into the game, Billy Mckay had a chance after 60 minutes as he met Nathan Shaw’s pass in the box but the striker’s effort was over the bar.
Caley Thistle did then pull one back through Charlie Gilmour as he got his first goal for the club. Luis Longstaff’s cross was clear into the path of Gilmour, about 30 yards out from goal, and he took a touch and smashed one past Josh Rae to make it 2-1.
The home side continued their pressure and went close through Wallace Duffy. The defender met Cameron Harper’s free-kick in the box but he headed over the bar after 71 minutes.
Caley Thistle were awarded a penalty after 77 minutes as Billy Mckay was brought down by Cameron Ballantyne in the box.
The striker stepped put and the penalty down the middle to draw the game level and also become the club’s all time leading goalscorer, surpassing Dennis Wyness’ longstanding record.
Caley Thistle pilled the pressure on in search on winner but it was Airdrie who won the game late on through Nikolay Todorov. The former Caley Thistle striker produced a fine finish from inside the box past Cameron Mackay after a good move from the visitors.
Caley Thistle looked to take the game to a penalty shootout as they went in search of an equaliser. Charlie Gilmour saw a shot from inside the box blocked on route to goal while Nathan Shaw saw a deflected effort somehow kept out by Airdrie keeper Joshua Rae.
The result ends Caley Thistle’s chances of progressing to the next round of the ViaPlay Cup as we face Dundee in our final group match on Sunday.