St Mirren's miserable season continued as they exited the William Hill Scottish Cup with a 2-1 defeat by Dundee United at the Simple Digital Arena in Paisley.
Tannadice striker Pavol Safranko scored after 15 minute and Robbie Neilson's Championship outfit had several opportunities to add to their lead in the first half of the last-16 tie before attacker Nicky Clark notched a second just before the interval.
Oran Kearney's side, three points adrift at the bottom of the Ladbrokes Premiership, looked bereft of belief and confidence but were offered hope in the 62nd minute when United's Calum Butcher was given a straight red card by referee Willie Collum for a high challenge on Ryan Flynn.
Striker Duckens Nazon's first goal for St Mirren, a deflected strike in the 77th minute, reduced the deficit but the 10-man visitors held out under mounting pressure to go into Monday night's quarter-final draw.
St Mirren, for all their efforts, have now lost five in a row despite extensively refurbishing their squad in the January transfer window and will wonder how the rest of their season will pan out.
Amid an energetic but untidy start to the match, United keeper Benjamin Siegrist made a comfortable save from midfielder Greg Tansey's long-distance drive.
It was the only real effort on goal until Safranko scored to turn the game in the visitors' favour.
Buddies keeper Vaclav Hladky had made a fine double-save, first from Clark's header from a Charlie Seaman cross, and then from the Slovak's close-range drive as he followed up.
However, when the loose ball was driven back towards goal by midfielder Peter Pawlett from outside the box, Safranko redirected the ball into the net from 12 yards for his 11th goal of the season.
Hladky then denied Safranko and Pawlett but in the final minute of the first-half the Paisley defence was again opened up by a long ball, this time by Jamie Robson, and Clark's finish, a perfectly-weighed chip over Hladky, was exquisite.
Kearney replaced Anders Dreyer and Tansey with Simeon Jackson and Kyle McAllister for the start of the second half
When Butcher deservedly departed for his tackle in the middle of the pitch, the home side almost capitalised immediately as defender Mihai Popescu struck the bar with a drive.
Neilson reshuffled his pack.
Osman Sow had replaced Cammy Smith before Morgaro Gomis came on for Clark and United defended desperately only to succumb to Nazon's drive from outside the box which took a nick and left Siegrist flatfooted as it sped past him.
St Mirren piled forward in the final stages and into five added minutes and United wobbled but they could not get the leveller, leaving the travelling support to salute their side at full-time.
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