Spurs have been knocked out of the FA Cup after a shock fifth round defeat to Sheffield United.
Antonio Conte's side are still waiting to win their first trophy since 2008 and were beaten by the Championship side courtesy of a fine goal from Iliman Ndiaye in the 79th minute.
Sheff United, who made a plethora of changes for the clash, have now reached the quarter-finals of England's oldest cup competition three times in the last four seasons and heaped more misery on Spurs.
Harry Kane came off the bench at Bramall Lane but was unable to make a difference as Spurs were dumped out by a Championship outfit for the second year on the trot.
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Spurs were beaten at the very same stage last season by Middlesbrough, who went through thanks to an extra time winner from Josh Coburn.
There were upsets aplenty at this stage of the competition, with Blackburn Rovers beating Leicester away from home on Tuesday night.
But the biggest shock came as League Two side Grimsby Town, currently 16th in the fourth tier, beat Southampton 2-1 at St Mary's courtesy of two penalties from Gavan Holohan.
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Their reward is a trip to high-flying Brighton later this month.
Sheff United, meanwhile, were drawn against promotional rivals Blackburn in the sixth round. They will be hoping to play in the semi-final at Wembley for the first time since 2014, when they lost 5-3 to Hull City.
Manchester United will host Fulham at Old Trafford, while Vincent Kompany will return to Manchester City as Burnley manager and lock horns with former boss Pep Guardiola at the Etihad Stadium.
Here is the draw in full:
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Man City vs Burnley
Man Utd vs Fulham
Brighton vs Grimsby
Sheffield United vs Blackburn
Topics: Tottenham Hotspur, Sheffield United, FA Cup