Ranking Tottenham’s 10 biggest Premier League flops

Unforgettable signings, but for all the wrong reasons

James Piercy

Now a model of Premier League stability, it wasn’t so long ago that Tottenham were the leading example of having to create something out of chaos.

While every club can lay claim to having their own worst set of signings, for a time, Spurs made more missteps in the market than they did in landing hits… particularly in one specific position.

Some outstanding footballers have passed through the doors of White Hart Lane since 1992 but our friends at Football Whispers have decided to count down Tottenham’s ten worst signings in the Premier League era.

10. Moussa Sissoko (2016-present)

Spurs had supposedly pulled off the bargain of the summer when they landed Sissoko from Newcastle for £30million in the wake of his excellent displays at Euro 2016. Except, the 29-year-old has never got anywhere near that level of performance, let alone even his best football at St James’ Park.

He still has time to impress but that familiar groan that accompanies his name on the team-sheet as fans dread another erratic and error-laded 90 minutes, is unlikely to ever go away.

And if anyone was smiling after that transfer it was Mike Ashley, smugly counting his cash.

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9. Vincent Janssen (2016-present)

Like Sissoko, he also theoretically has time to make something of his Spurs career but it will take a lot because, at this moment in time, Janssen looks as far away from the first XI as he did when he was at AZ Alkmaar.

The money factor also comes into this selection as, while six goals in 36 games is particularly poor, it’s even worse when stacked up against his £17million fee. Janssen cannot help that his loan spell at Fenerbahce last season did little is discount the theory that he’s just simply out of his depth at this level.

8. Kevin-Prince Boateng (2007-09)

‘The Ghetto Kid’, as he was first branded, arrived in London against a wave of hype but was a classic example of a club not properly looking after its assets or misunderstanding the personality of the individual they had signed.

Boateng admits the nightlife of the big city affected his commitment and left him unfit and under-motivated. Much of that is his fault but with subsequent moves to Milan and Schalke showing what a player he can be, it’s a huge case of what should have been for the Ghanaian at Spurs.  

7. Serhiy Rebrov (2000-04)

Manchester United may have won the Champions League in 1998/99 but it was Dynamo Kiev who truly captured the hearts of Europe, led by their dynamic front duo of Rebrov and Andriy Shevchenko. With Shevchenko then proving a star at AC Milan, landing his partner was seen a major coup for Spurs.

But the Ukrainian was just an awful fit for English football and a real damning indictment of the scouting department of the time as while he was a ‘big name’, his eventual return of 15 goals in 75 games really wasn’t worth all the excitement.  

6. Paulinho (2013-15)

Sometimes the right player is just at the wrong club at the wrong time with the wrong coach. No truer an example is of Paulinho who, although back in China, was excellent for Barcelona last season and remains a lynchpin of Tite’s Brazil squad.

If anything, his success vindicates the decision to bring him to England but, at the same time, also begs the question as to why Tottenham couldn’t get the best out of him and makes his signing from Corinthians look even worse.  

5. Grzegorz Rasiak (2005-06)

The Championship is now a safer environment for Premier League clubs to explore potential squad additions but 10 years ago players such as Rasiak were responsible for England’s second tier being snubbed by the big boys.

A deadline day signing from Derby as Spurs sought attacking reinforcements, the Pole was too slow, had a poor first touch, was poor in the air despite being signed as a target-man and looked bereft of confidence whenever called upon by Martin Jol. Admittedly, that was only eight times in the Premier League, which tells you all you need to know.

4. Paolo Tramezzani (1998-2000)

Arsenal’s success in the mid to late 90s was enhanced by the utter mess Tottenham were at the time as a revolving door of average players and coaches essentially left them a glorified mid-table club.

Few exemplified how forgettable they were than Italian defender Tramezzani, who was remarkably Spurs’ only summer signing in 1998. He possessed a snazzy name and haircut and looked nice on the ball but the patience on the ball ingrained in him from his Serie A days was totally inappropriate for the smash, bang, wallop of the Premier League at the time.

3. David Bentley (2008-13)

Briefly the new golden boy of English football, Bentley’s £15million transfer from Blackburn seemed a logical progression after two good seasons at Ewood Park and great piece of business. That feeling was only enhanced by a sensational goal in the North London Derby in the 4-4 classic.

However, that was as a good as it got as the revelation soon dawned that Bentley lacked the requisite desire and interest in football to truly make it. Five years he was paid handsomely but only two of them were in a Tottenham shirt due to his drastic drop in form.

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2. Helder Postiga (2003-04)

Scoring 19 goals as a 20-year-old striker in a treble-winning season ( is always going to get you noticed but Postiga’s move to Spurs was a case of too much, too soon and proved yet another giant flop in the file marked ‘strikers’.

The Portuguese just wasn’t ready for the transition from his homeland to England and managed one goal in 19 Premier League appearances. Postiga lacked pace and in the Premier League then, if that was the case the only other option was to be a battering ram of a forward. Unsurprisingly, that role was unsuitable for a kid fresh out of Lisbon for the first time.

1.Roberto Soldado (2013-15)

The Spain striker isn’t the worst player on this list, and he arguably performed better than many of the forward previously mentioned but his inclusion at No1 is weighted considerably by his transfer fee – a bright and shiny, club record £26m.

That was funded by the sale of Gareth Bale but Soldado never come close to filling the goal void left by the Welshman’s departure with just two from open play in his debut season. Another individual who arrived with an excellent CV but proved completely unfit for English football, unlike his many predecessors though, he cost a considerable amount of money.

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