Ross County were eliminated from the Betfred Cup following a 3-2 extra-time defeat against 10-man Motherwell in the last 16.
Motherwell had grabbed the initiative on 50 minutes when Gael Bigirimana lashed home from close-range.
Former Caley Thistle attacker Alex Fisher spurned a glorious chance to finish the tie shortly after coming on as a substitute, with the Staggies making his side pay on 65 minutes through Alex Schalk.
Motherwell regained the lead three minutes into extra-time thanks to Chris Cadden’s strike, however Craig Curran levelled from the spot after being hauled down in the box by Charles Dunne, who was red carded.
Ross MacLean’s strike on 112 minutes ensured the Steelmen advanced however, setting up a quarter-final tie at home to Aberdeen.
County gained a timely boost ahead of kick-off, by completing the signing of midfielder Ross Draper from rivals Caley Thistle, however there was no quick introduction to playing action, with the Englishman still to complete his medical.
While the signing of Draper prompted further gloating from Staggies supporters, who have enjoyed the demise of their recently-relegated Highland rivals, Jim McIntyre’s men had to quickly get down to business ahead of their last-16 tie with the Steelmen.
The Staggies remained unchanged from the side that got the league campaign off to a flying start with Saturday’s 2-1 win against Dundee, with County aiming to keep momentum going by extending their unbeaten run of 13 matches.
The Betfred Cup brought the Staggies an early opportunity to atone for an abrupt exit from both cup competitions last season, most notably their failure to make it past the group stage of last season’s League Cup competition.
County looked to hit the front foot, with both Michael Gardyne and Christopher Routis seeing powerful efforts blocked within the opening minute, while at the other end Motherwell’s first threat came when Craig Tanner nodded Chris Cadden’s cross wide.
McIntyre was forced to make an early change when Tim Chow suffered a head injury in a collision which saw he and skipper Andrew Davies attack the same ball, with Jim O’Brien introduced after 13 minutes.
Despite decent starts from both sides, neither was able to follow it up with a sustained spell of pressure, with both goalkeepers untested in the opening half-hour.
A well-worked corner should have brought the Steelmen the opening goal on 33 minutes, in the best chance of the first-half. Gael Bigirimana’s low corner to the front post picked out the untracked run of Louis Moult, however the normally prolific attacker steered his first-time effort harmlessly over with the full goal to aim at.
County created a decent opening on 40 minutes when Routis nodded the ball into the path of Jamie Lindsay, however the shot did not sit kindly for the on-loan Celtic midfielder, who steered his effort over.
The Staggies’ best chance of the first-half arrived moments later however, as Marcus Fraser’s well-placed ball over the top released the run of Lindsay down the right flank, with his cut-back diverted goalwards from six yards by Alex Schalk, only for Motherwell goalkeeper Trevor Carson to show superb reflexes to turn it behind.
Motherwell also threatened before the break, as Tanner’s corner picked out Moult at the far post, with the attacker nodding over under pressure from a cluster of home defenders.
Motherwell grabbed the lead just five minutes into the second-half however. The impressive Tanner broke with the ball down the right flank, with Davies going to ground allowing him to send his cross into the middle, where Moult nodded the ball into the path of the onrushing Bigirimana who hammered high past Fox from 10 yards.
The goal brought about a response from the Staggies and they nearly levelled within three minutes, when Routis’ header picked out Jason Naismith at the far post, but he guided it wide under pressure from Motherwell defender Charles Dunne.
Schalk should have levelled on 58 minutes with a gilt-edged opportunity that fell his way, when he tried to turn Davies’ already goalbound header from Gardyne’s cross into the net from point-blank range, only to divert it over.
The miss could have proven so costly. Former Caley Thistle attacker Alex Fisher, on as a substitute was initially desperately unlucky to be denied a goal when his shot on the turn was blocked by a strong hand from Scott Fox, however the Englishman somehow managed to send his follow-up effort wide from close-range. A moment which could have finished the tie.
County took full advantage on 65 minutes, with Schalk this time making no mistake. The chance came his way thanks to O’Brien’s superb threaded pass through the middle, with the Dutch attacker using his pace to charge beyond the last Motherwell defender before clipping the ball past Carson from 12 yards.
Fisher was denied again on 80 minutes when he saw his header hacked off the line by Gardyne, however extra-time was required.
Motherwell regained the lead three minutes into extra-time, when Dunne’s header from Fisher’s cross came back off the crossbar, before being bundled home by the impressive Cadden at the far post.
County were awarded a penalty on 103 minutes when substitute Davis Keillor-Dunn’s was blocked into the path of Craig Curran, who was tugged down at the far post by Dunne, resulting in the defender being red carded, with Curran making no mistake from the spot.
Motherwell snatched the lead on 112 minutes when Cedric Kipre’s through ball found the run of substitute Ross MacLean, and despite claims for offside, he showed excellent composure to round Fox and slot home for what proved to be the winner.