Since Daniel Levy arrived at the club in 2001, Tottenham Hotspur have won one solitary piece of silverware, the League Cup in 2008.
Juande Ramos was in charge of Tottenham at the time, Jonathan Woodgate won the player of the match award in the final and Steed Malbranque was in midfield for Spurs – it was a long time ago.
Ange Postecoglou is now the man tasked with ending that rot, a manager who will be relieved that both Djed Spence and Brennan Johnson scored late goals against Coventry City.
Postecoglou has often spoken about his desire to win trophies and compete for everything possible during his time in N17, a target that is looking slightly more challenging this season.
That being said, with James Maddison in excellent form for Tottenham, anything can still happen.
Daniel Levy omits Luka Modric from his top three players at Tottenham
Speaking at a fan forum via the Evening Standard, Levy has now suggested who his favourite three players have during his time in charge at Spurs.
The chairman was first asked about his stand out moments from those 21 years in charge, and then went on to mention three legendary Tottenham names.

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Levy said: “Clearly, getting into the Champions League Final [and] I think opening this stadium is a great legacy for this club.
“The third one is a really difficult one because we’ve had a lot of great players at this club and I’ve had the honour of employing a lot of them.
“So I couldn’t single out one player but Gareth Bale, [Dimitar] Berbatov, Harry Kane, we go on.”
Dominic Solanke hoping to emulate Dimitar Berbatov in N17
Of course, Tottenham fans will be hoping that Levy is one day reflecting on the signing of Dominic Solanke in a similar way – the club’s new record deal.
Maddison was amazed by Solanke against Brentford, a striker who already seems as if he has a lot to prove in north London.
Solanke actually arrived at Spurs in fairly similar circumstances to Berbatov once did in 2006.
Both had scored 21 goals for their old clubs the season before, and both were just about entering their late twenties – Solanke being 27 and Berbatov 25.
That being said, Solanke will probably be hoping to eclipse the Bulgarian’s 46 goals for the club, even if he may be happy to initially reach that number in Berbatov’s 102 games.
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