Managers such as Harry Redknapp, Mauricio Pochettino and Jose Mourinho have all had a crack at winning some silverware in recent years.
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But none of the bosses have been able to end the trophy drought or win the Premier League.
This season, Spurs are well out of the title race and have been knocked out of the Carabao Cup, FA Cup and Champions League, with their long wait for a trophy set to continue.
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.
This trophy drought is set to be extended after the north Londoners were knocked out of the FA Cup by Championship side Sheffield United earlier this season.
Tottenham's only hope of success after that came in the Champions League, however, they went on to lose to AC Milan over two legs in the round of 16.
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Have Tottenham ever won the Premier League?
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.
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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.
The Lilywhites then went one place better the season after, coming second behind Antonio Conte's Chelsea.
Conte was then unable to bring that success to Spurs and was sacked in March before being replaced by his assistant Cristian Stellini until the end of the season.
Stellini will see out the campaign as Tottenham once again are set to go without any silverware.
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