An extra-time goal from substitute Moses Ebiye edged Motherwell past Kilmarnock and into the quarter-finals of the Premier Sports Cup, where they will host Dundee United.
Stuart Findlay’s red card five minutes after the interval swung things in the home side’s favour after a first half that failed to yield many chances.
Motherwell could not make their numerical advantage count in regulation time, but debutant Tawanda Maswanhise teed up Ebiye six minutes into extra time for the goal that proved decisive.
Kilmarnock made nine changes from the team that triumphed against Tromso in Norway on Thursday in Conference League qualifying, and it was the visitors who had the first meaningful sight of goal, Marley Watkins dragging his effort wide after a promising counter-attack.
Fraser Murray won possession and worked his way to the byeline, delivered a cross that Motherwell keeper Aston Oxborough came for but failed to reach, only for Watkins to miss the target with his header.
After failing to offer much in an attacking sense in the first half, Motherwell emerged from the break and immediately upped the tempo, Ewan Wilson and Zach Robinson both forcing saves from Kieran O’Hara.
The visitors suffered a blow five minutes into the second half when Findlay was sent off for a second bookable offence after an ill-advised lunging tackle on Paul McGinn.
Derek McInnes responded by making five substitutions, while Motherwell threw on Tony Watt and Maswanhise for debuts as they looked to find the opening goal. Watt squandered the best chance of the game when he sent a header from just six yards out over the bar.
The home side finally found a way through when the lively Maswanhise dinked an inviting cross towards fellow substitute Ebiye, who guided his header from 10 yards past the despairing dive of O’Hara and into the net.
It was probably merited given the balance of play from the Findlay red card onwards and Motherwell move into the last eight, while Kilmarnock’s attention switches back to Europe and a trip to Copenhagen on Thursday.
Maswanhise a promising addition; Findlay red costs Killie
Motherwell’s challenge this season was always going to be replacing the goals and attacking focal point they lost with the departure of Theo Bair.
On this evidence they are not quite there yet. Some of their play back-to-front was good, but when it came to that final third they often seemed devoid of ideas.
That was until the introduction of Maswanhise for his debut in the second half. The Zimbabwe international gave Motherwell a different dimension, asking questions of the Kilmarnock defence with his pace and ability to go on to either foot. He looked very promising.
Watt also came on for his first appearance since returning on loan from Dundee United. He received a few jeers from home supporters still sore at the manner of his departure for Tannadice two years ago, but a few goals – he missed a great chance when he came off the bench – should silence any doubters.
Extra time is the last thing Derek McInnes would have wanted for his Killie players after their exertions in Europe last week in Norway and coming up this Thursday in Denmark.
Having made nine changes, his side did not appear overly tired, but they did look disjointed and failed to reach the level we know they are capable of. Findlay’s red card left them with an uphill task.
McInnes has always placed a premium on good cup runs and while this last-16 exit will sting for now, a positive result in Copenhagen and another step towards the Conference League would more than make up for it.
What they said
Motherwell manager Stuart Kettlewell: "We're deserving of it. We were okay when it was 11 v 11 without setting the heather alight. We were reasonably confident.
"They gave up a bit of pressure [after the red card], invite us into crossing positions, the final third. We could have done better with capitalising on that.
"We know we can get better and we'll need to be better. We've had a lot of issues with injuries but we had to get into the next round of the cup and we did that."
Kilmarnock manager Derek McInnes: "That was so tough on each and every one of us.
"It was always my intention to make three or four changes at 55 minutes or so but when Stuart [Findlay] got sent off, it was all hands to the pump. We felt the players needed help out there.
"It was such a gutsy performance. I love managing this group of boys because when more was needed, they gave it. We still carried a fight, we didn't accept what was happening. I couldn't have been more proud of them."