St Mirren have been eliminated from the Scottish League Cup with a group game to spare, while Premiership rivals St Johnstone also face an early exit from the competition as League 2 Annan Athletic became the first team to progress.
St Mirren, tournament winners in 2013, fell to their second defeat in three outings, with Justin Devenny and 16-year-old substitute Kyan Gunn on target for League One Airdrieonians.
The Paisley side lost Greg Kiltie to a first-half red card when he caught Euan Deveney on the head with a high boot.
Airdrie go to Arbroath next and must win to overhaul the Group E leaders.
St Johnstone, who completed a remarkable cup double in 2020-21, won 4-2 at Elgin City but cannot catch unbeaten Annan in Group F.
The Perth side can reach eight points if they beat Ayr United on Saturday but that tally is highly unlikely to be enough for one of the three best runners-up spots.
Annan, who were trailing 1-0 and down to 10 men, were looking for a point in their final game and levelled at home to Ayr thanks to a 95th-minute penalty from Tony Wallace, going on to take another bonus point in the shoot-out.
Aberdeen continue to build good momentum as the impressive Vincente Besuijen scored twice in a 5-0 win at Stirling Albion.
Jonny Hayes set up close-range finishes for Christian Ramirez and Ross McCrorie, with Matty Kennedy curling home a free-kick to take Jim Goodwin’s side on to nine points, with a home game against nearest rivals Raith Rovers to come on Sunday.
Ross County climbed to the top of Group C thanks to a 2-0 win at Alloa Athletic.
Kazeem Olaigbe crossed for Josh Sims to nod in at back post and Jordy Hiwula rounded the keeper with the last kick of the ball. Connor Sammon squandered the chance to equalise before the interval when his weak penalty was saved by Jake Eastwood.
Inverness Caley Thistle took control of Group G with a 4-0 win at home to Albion Rovers. Billy Mckay headed in an early cross from Daniel Mackay before Cameron Harper pinged a free-kick into the top corner. Wallace Duffy struck early in the second half and Harper added another for the Highlanders.
Dundee and Partick Thistle are other Championship sides who moved on to maximum points from three games.
Alex Jakubiak kept a cool head following a penalty box scramble to open the scoring at Ochilview and Cammy Kerr lashed a rocket into top corner.
Louis Longridge thumped in a reply for Queen’s Park but the Dark Blues held on and will aim to be a seeded section topper when they take on Forfar at Dens Park on Saturday.
Thistle dominated against Highland League side Fraserburgh at Firhill and a low cross from Jack McMillan was turned into his own net by Bryan Hay. Brian Graham then applied an emphatic finish to Kevin Holt’s delivery.
Ian McCall’s side now know they will hang on to first place ahead of Kilmarnock if they beat Montrose in Glasgow at the weekend.
Scottish League Cup results:
Dumbarton 0-0 Raith Rovers (2-3 pens)
Stirling Albion 0-5 Aberdeen
Montrose 0-2 Stenhousemuir
Partick Thistle 2-0 Fraserburgh
Alloa Athletic 0-2 Ross County
East Fife 3-2 Buckie Thistle
Airdrieonians 2-0 St Mirren
Annan Athletic 1-1 Ayr United (5-4 pens)
Elgin City 2-4 St Johnstone
Cove Rangers 2-3 Kelty Hearts
Inverness CT 4-0 Albion Rovers
Forfar Athletic 2-2 Stranraer (5-3 pens)
Queen’s Park 1-2 Dundee