Cove Rangers were beaten 2-1 by 10-men Livingston as the Premiership side came from behind to win at the Balmoral Stadium.
The visitors were left a man short in the first-half when Esmael Goncalves was dismissed for violent conduct, with Iain Vigurs giving Cove the lead just before the break.
David Martindale’s men were level at the start of the second half through Andrew Shinnie before Nicky Devlin snatched a late winner for Livi.
It keeps the Lions’ hopes of qualifying for the knockout stage alive, while Cove need to win at home to Kelty Hearts on Tuesday.
Cove made three changes from the 2-1 win at Albion Rovers, with Kyle Gourlay, Mark Reynolds and Leighton McIntosh dropping out for Stuart McKenzie, Morgyn Neill and Iain Vigurs.
Livingston lost their second group game in midweek to Caley Thistle and tested McKenzie early, with a Sean Kelly free-kick forcing the Cove stopper to punch clear.
The home side had looked bright in spells and fashioned a chance for midfielder Connor Scully, who flashed a shot just wide after Mitch Megginson played him in.
Cove were given a huge advantage on 24 minutes when Goncalves inexplicably lashed out at Scott Ross, kicking the Cove defender off the ball. Referee Willie Collum was on the spot to issue a red card.
However it was the visitors who threatened the target next. Full-back Cristian Montano surged forwards, covering at least 50 yards through the middle of the pitch, before releasing Dylan Bahamboula. The former Oldham man worked a shooting angle for himself but his effort rolled agonisingly past the far post.
Cove took the lead in first-half stoppage-time, when Fraser Fyvie’s short corner to Shay Logan was only cleared to the edge of the box. It fell to Iain Vigurs, who struck sweetly on the half-volley to find the bottom corner.
It took Livingston less than three minutes of the second half to level though, with a half-cleared corner scuffed across goal by Ayo Obileye where Shinnie was able to dive in and prod home.
The hosts were desperate to reclaim the advantage and Scully twice came close to doing so.
A well-worked move saw Vigurs pick out Megginson, who nodded the ball down to Scully on the edge of the box. He timed his strike perfectly but Ivan Konovalov was able to gather.
Vigurs was becoming an increasingly influential figure and his long ball picked out Scully in behind the Livingston defence. However as he was shaping to shoot, Fyvie came across his path and the chance was lost.
Konovalov got down to turn away an effort from Megginson at his near post and after Robbie Leitch showed sharp footwork, he could only bury the ball into side netting.
Ultimately Cove would be punished for it with three minutes to go, with Stephane Omeonga releasing Devlin on the counter-attack and the captain expertly finished across McKenzie with his weaker foot.