Managers such as Harry Redknapp, Maurico Pochettino and Jose Mourinho have all had a crack at winning some silverware in recent years.
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But no one has been able to end the trophy drought or win the Premier League.
Antonio Conte's arrival was meant to change everything, but as of yet, the Italian's new-look Spurs are yet to mount a serious title challenge or push for silverware.
When was Tottenham's last trophy and how many have they won?
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Tottenham's last trophy came 15 years ago in 2008.
They lifted the League Cup (now the Carabao Cup) for the fifth time after beating Chelsea 2-1 in extra time at Wembley.
Jonathan Woodgate scored the winner after Didier Drogba gave Chelsea the lead.
At the time, this was Spurs' first trophy in nine years, with all of their previous honours coming before 2000.
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In total, the Lilywhites have won 26 trophies in their history, including two UEFA Cups and eight FA Cups.
But that trophy drought is set to be extended after the north Londoners were knocked out of the FA Cup by Championship side Sheffield United.
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Have Tottenham ever won the Premier League?
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Tottenham have never won the Premier League.
They came closest in the 2015/16 and 2016/17 seasons, finishing third and second in those campaigns respectively.
In 2016, Spurs had chased Leicester down for the title and were favourites to lift the trophy during the season with the Foxes expected to drop off.
Of course, Leicester managed to hold on to clinch an incredible title win as Pochettino's side struggled in their last few games, dropping below rivals Arsenal into third.
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The Lilywhites then went one place better the season after, coming second behind Conte's Chelsea.
Now the Italian is in charge of Spurs, they will be hopeful that they can finally achieve what they have never done before in the near future.
But considering they are 15 points behind Arsenal at the top of the table, it seems unlikely they will be winning the Premier League this season.
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