Ross County started their League Cup campaign with a 5-4 penalty shoot-out victory following a 3-3 draw at Links Park.
The Staggies were three up against the Gable Endies courtesy of goals from Oli Shaw, Billy Mckay and Regan Charles-Cook.
But the Angus side rallied with two quickfire second half goals before Andrew Steeves equalised in the 89th minute to force a shoot-out, with Montrose striker Martin Rennie hitting the crossbar with the 10th penalty to give the Dingwall side a bonus second point.
Having been in command, the Staggies will be left to wonder how they ended up with only two points from this Group D opener rather than all three.
County handed a first start to Jermaine Hylton – who signed last week from Motherwell – he was among six changes to the team defeated 2-0 by Rangers on Sunday with Keith Watson, Carl Tremarco, Iain Vigurs, Mckay and Shaw also drafted into the starting line-up.
Montrose started in lively fashion, but a quickfire double from the Staggies put them on the backfoot.
The first came on 13 minutes with Hylton and Harry Paton combing down the left to set up Mckay and his strike from the edge of the box was helped into the net by Shaw.
Two minutes later Mckay doubled the lead heading home from close range after Gable Endies goalkeeper Allan Fleming had parried Regan Charles-Cook’s strike from the right side of the area.
Paton was a livewire in County’s midfield with his surges forward and incisive passing a threat to the home side.
However, Montrose also showed plenty of attacking intent and hit the woodwork twice around the half hour mark.
Sean Dillon almost caught out goalkeeper Ross Laidlaw with a lob from his own half, but the ball hit the crossbar and moments later Cammy Ballantyne’s effort from 25 yards was tipped onto the left post by Laidlaw.
County looked to have secured the points just six minutes into the second half with Charles-Cook firing home a fine third goal from 20 yards after weaving in from the right flank.
However, Montrose rallied with Graham Webster heading home Martin Rennie’s cross from left on 62 minutes and Callum Morris deflecting a Cammy Ballantyne shot from the edge of the box beyond Laidlaw five minutes later.
In between Mckay hit the crossbar with a bar before Aidan Quinn blocked his effort on the rebound.
With little over quarter of an hour left Morris headed against the left post from Paton’s clipped cross.
But Montrose kept pushing and equalised with a minute left when Steeves fired home after a Rennie cross caused problems for the County backline.
Ross Stewart, Mckay, Paton, Gardyne and Lakin converted County’s spot-kicks with Webster, Steeves, Lewis Milne and Ross Campbell doing the same for Montrose before Rennie hit the bar.