Kilmarnock edged through to the quarter-finals of the Scottish Cup with a narrow win over Dundee United at Tannadice.
Kyle Vassell netted what proved to be the winner in the second half with his first goal for the club.
United’s misery was made complete when debutant, on-loan Huddersfield defender Loick Ayina, was sent off late on.
Prior to kick-off there was a minute’s applause for Dundee United great and former Kilmarnock coach Billy Thomson, who died this week.
After a cagey opening there was a half-hearted appeal for a penalty from Kilmarnock in the 11th minute when Danny Armstrong fell to the turf under a challenge from United defender Scott McMann inside the box but referee Alan Muir saw no offence.
There was an even bigger penalty shout shortly after when a ball from Brad Lyons appeared to strike McMann’s arm but again no spot-kick was awarded with VAR not in operation at the game.
As the half progressed, both sides were struggling for fluency with the keepers having little to do.
The first yellow card of a scrappy encounter arrived on the half-hour mark when McMann clattered into Armstrong with Ayina swiftly following him into the book after a late challenge on Lyons.
There was finally a shot of note in the 40th minute when Killie skipper Rory McKenzie hit a low long-range effort that United keeper Mark Birighitti dived to turn around his right-hand post.
However the teams headed down the tunnel at half-time with the game still deadlocked.
Five minutes after the restart, United were shouting for a penalty when the ball appeared to strike Joe Wright’s arm and then Craig Sibbald hit a shot from the edge of the box with Killie keeper Sam Walker making a fine diving stop.
The home side’s tails were up and, shortly after, Glenn Middleton delivered a cross from the left towards Liam Smith with the defender’s header clipping the top of the crossbar.
However, it was the visitors who finally broke the deadlock in the 55th minute when Armstrong swung a corner in from the right with Vassell rose highest to beat Birighitti and power a header home.
United were reduced to 10 men in the 78th minute when Ayina fouled Vassell, with the referee flashing a second yellow card followed by a red.
Despite that, the Tangerines came agonisingly close to equalising when sub Aziz Behich smacked a long-range shot off the crossbar.