Middlesbrough produced another FA Cup shock to extend Tottenham’s long wait for silverware with a 1-0 win after extra time at the Riverside on Tuesday, while Manchester City eased into the last eight with a 2-0 victory at Peterborough.
Boro knocked out Manchester United at Old Trafford in the fourth round and the Championship side were worthy winners to condemn Spurs to another trophyless season.
Not since a League Cup win in 2008 have Tottenham lifted a trophy and another hugely disappointing defeat poses further questions over the future of manager Antonio Conte.
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The Italian only took charge in November but has already hinted he could walk away after a run of four defeats in the past six Premier League games.
Teenager Josh Coburn came off the bench to score the only goal with a thumping finish across Hugo Lloris in the 107th minute.
Chris Wilder’s men might not have been forced to play the extra 30 minutes had Matt Crooks connected with a free header from a corner.
Harry Kane did have the ball in the net for Tottenham only to be flagged offside.
But the England captain may also be again considering his future as he waits to win the first major honour of his career.
Middlesbrough was by far the brighter side in extra time and got their reward when Coburn rifled across Lloris from Crooks’ through ball.
Earlier, Oleksandr Zinchenko captained City as classy finishes from Riyad Mahrez and Jack Grealish sent the English champions through.
Crystal Palace also booked their place in the quarterfinals with a 2-1 win over Stoke.
Cheikhou Kouyate and Jairo Riedewald struck for the Eagles on either side of Josh Tymon’s equaliser. (Supersport)
