Kane, Le Tissier, Di Natale: Who is the best footballer never to win a trophy?
Tottenham and Harry Kane are out of the FA Cup after crashing out to Championship side, Middlesbrough, on Tuesday night.
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Folarin Balogun rinsed Tottenham's Cristian Romero with brilliant skill
Arsenal loanee Folarin Balogun would have enjoyed helping Middlesbrough knock Tottenham Hotspur out of the FA Cup.
Tottenham ratings vs Middlesbrough: Doherty 7, Romero 6, Kane 5, Son 4
Antonio Conte has vowed to continue to try to improve Tottenham Hotspur after they were dumped out of the FA Cup at Middlesbrough.
Middlesbrough Shock Tottenham, Manchester City Ease Into FA Cup Quarters
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.
Conte vows to improve Spurs after shock Cup loss to Middlesbrough
Antonio Conte insists he has the patience to see the job through at Tottenham after they were dumped out of the FA Cup at Middlesbrough. The Championship side followed up their fourth-round giant-killing of Manchester United with another Premier League scalp as teenager Josh Coburn's extra-time goal earned a deserved 1-0 win at the Riverside Stadium. It was an abject display by Spurs, who were condemned to yet another season without a trophy and their campaign hinges on their ability to produce a late surge into the top four.
Antonio Conte vows to keep working to improve Tottenham after FA Cup shock
Antonio Conte insists he has the patience to see the job through at Tottenham after they were dumped out of the FA Cup at Middlesbrough.
Middlesbrough claim second Premier League scalp as Josh Coburn sinks Tottenham
Teenager Josh Coburn was the hero as Middlesbrough produced another FA Cup upset by knocking out Tottenham with a 1-0 extra-time victory in the fifth round.
Tottenham stunned by Middlesbrough in FA Cup upset - in pictures
Teenager Josh Coburn was the hero as Middlesbrough produced another FA Cup upset by knocking out Tottenham with a 1-0 extra-time victory in the fifth round.