Tottenham Hotspur have certainly given us some Spursy moments over the years on the pitch but what about off it and in the transfer market?

Well, things have been just as comical at times with the Lilywhites there too. They may have recently enjoyed a pretty successful period in their history, their transfer strategy remains a little suspect to say the least. They even became the first Premier League team to go two transfer windows without making a single signing.

But when they have made signings, Spurs have often made many mistakes along the way.

Here’s their 20 worst signings of the Premier League era…

Gilberto

Of the two Gilberto da Silvas to have plied their trade in north London, Tottenham certainly had the lesser one in Gilberto da Silva Melo.

The left-back turned up at White Hart Lane initially in January 2008 with some pedigree in the form of 30 Brazil caps and four strong years in Germany with Hertha Berlin but could never adapt to the pace of the Premier League and left in July 2009 a complete flop.

Sergei Rebrov

The first of a fair few strikers to feature on this list, Ukraine legend Sergei Rebrov managed a mere 16 goals in a depressing four-year spell with the Lilywhites.

What makes it worse is that Glenn Hoddle threw away a gut-busting £11m, we are talking in 2000, to bring him in based on his form with Dynamo Kyiv – although it’s far from the last waste of money we’re going to be looking at today.

Paolo Tramezzani 

Speaking of foreign players who just couldn’t get to grips with English football, Paolo Tramezzani was a calamitous left-back if there ever was one.

Pictured above with fellow Italian Premier League failure Nicola Berti who’s bizarrely wearing a t-shirt from the Four Seasons hotel in New York to training, Tramezzani would make just six forgettable appearances in north London.

Bobby Zamora

Bobby Zamora would go onto enjoy an accomplished Premier League career with the likes of West Ham United, Fulham and Queens Park Rangers, but not before his own sorry spell at the Lane.

The Lilywhites were the team to give the future England man his big break when they signed him for Brighton & Hove Albion for a lofty £1.5m in summer 2003, however, he would only contribute the one goal for Spurs before being shipped off as part of the deal that saw the legendary Jermain Defoe arrive in N17.

Mbulelo Mabizela 

Remember him?

Prior to the 2003/2004 season, the Lilywhites decided to sign ill-disciplined centre-back Mbulelo Mabizela based on a performance he put in for Orlando Pirates against them in a friendly, it worked out just about as well as it sounded it would.

David Bentley

What did David Bentley ever really do in a Spurs shirt apart from score THAT goal against his former club in the North London derby?

Well, you could list any number of hilarious off-field pranks and incidents.

But it’s what happens on the pitch that really matters and the ex-Three Lions star never really lived up to his potential or his £15m price tag at White Hart Lane before bizarrely retiring at the age of 29.

Bongani Khumalo 

The picture above more or less sums up Bongani Khumalo’s Tottenham career, as the former South Africa captain looked so out of his depth on loan at the likes of Preston, Doncaster and Colchester and in matches for the reserves that he somehow managed to not make a single competitive first-team appearance for the entirety of his four-and-a-half-year spell.

Spurs haven’t had much luck with South Africans, have they?

Roberto Soldado

A striker who doesn’t play too badly and works hard for the team but is also hampered with an uncanny inability to score goals, sounds odd, though Roberto Soldado was that very thing for Tottenham.

It will still send shivers down the spine of Spurs fans that their club flushed £26m of their Gareth Bale money down the toilet on the Spaniard for him to score 16 times in 76 games for them.

Need we say anything more?

Calum Davenport

When the Lilywhites beat others in the race to sign England U21 international defender Calum Davenport from Coventry City in 2004, they would have thought they’d unearthed a real £1.3m gem.

However, the centre-half embarked on a bizarre career that would never see him get close to the level he was once thought to have the potential to reach – he appeared a mere 20 times for Spurs.

Paulinho

After an impressive 2012/2013 campaign for Corinthians in his native Brazil, Paulinho was noticed in Europe by Andre Villas-Boas and another chunk of the Bale money would be allocated to obtain his signature.

It would take the Lilywhites two seasons to work out the Brazil man just wasn’t up to Premier League standard after he was only able to register nine-goal involvements in 45 matches and he was disposed of by Mauricio Pochettino in one of the early lucrative Chinese Super League transfers.

Members of the Tottenham faithful will most recently remember him being oddly brought back to the continent in 2017 by Barcelona.