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.
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.