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Sheffield United damaged Tottenham's bid to qualify for the Champions League and rekindled their own European ambitions after surviving a VAR controversy in their 3-1 win on Thursday.
Chris Wilder's side took the lead through Sander Berge's first half strike at Bramall Lane.
But Tottenham were denied an equaliser moments later when Harry Kane's goal was chalked off by VAR for a dubious handball against Lucas Moura.
Lucas appeared to have the ball kicked against his arm in the build-up to Kane's strike and Tottenham manager Jose Mourinho complained angrily on the touchline.
Lys Mousset and Oli McBurnie rubbed salt into Mourinho's wounds as they both netted for United after the interval.
Kane's last minute goal was no consolation for Tottenham, who are now in grave danger of missing out on next season's Champions League.
They sit nine points behind fourth placed Chelsea and seven adrift of fifth placed Manchester United after their first defeat since the restart.
The Blades, winners for the first time in five games following the hiatus, moved two points above Tottenham into seventh place, keeping alive their hopes of qualifying for European action.
United had not managed more than one shot on target in any of their previous three Premier League matches, going without a goal on each occasion.
It took less than 60 seconds for George Baldock to get an effort on target, but Tottenham keeper Hugo Lloris dived to his left to make the save.
Tottenham responded when Eric Dier flashed a header just wide, with Moussa Sissoko stretching in vain to reach it at the far post.
Kane couldn't hit the target from Steven Bergwijn's pass and Tottenham were punished as Berge put the Blades ahead in the 31st minute.
After spreading the ball wide to Chris Basham, Berge broke into the Tottenham area, collected the return pass and drilled his low shot into the far corner.
It was the Norway midfielder's first goal since his January move from Genk.
Tottenham thought they had equalised two minutes later as Lucas sprinted forward and, despite being pushed over, managed to knock the ball onto Kane, who cut inside and fired home.
Kane's celebrations were curtailed when VAR disallowed the goal for a handball by Moura, who had the ball kicked against his arm as he tumbled under pressure from several United players.
Mourinho was disgusted with what appeared to be an extremely harsh decision and his mood wasn't improved when already-booked United midfielder Oli Norwood escaped a red card for elbowing Son Heung-min.
Tottenham were struggling to find their rhythm and United nearly doubled their lead when David McGoldrick shot into the side-netting early in the second half.
Ben Osborn was making his first Premier League start and the United midfielder had a key role as they struck again in the 69th minute.
Breaking into the area, Osborn's deft pass picked out Enda Stevens and he squared for the unmarked Mousset to slot home from close-range for his first goal since December.
McBurnie put the result beyond doubt when he tapped in from Berge's cross in the 84th minute after more sloppy Tottenham defending.
Kane had scored against 28 of 29 teams he has played against in the Premier League, with United the only ones to hold him in check.
He got off the mark against them with a simple finish from Son's pass, but his 199th career club goal was far too late to avoid a painful defeat.
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