Tottenham failed to get their top four challenge back on track, with a dour 0-0 draw against Burnley on Sunday lunchtime.
Mauricio Pochettino’s side trail fourth placed Manchester City by eight points, and look set to rival Liverpool for that fifth spot – and Europa League qualification.
It should still go down as a season of progression under the Argentine however.
Harry Kane has established himself as one of the most exciting young talents in Europe, with the forward having scored 29 goals in all competitions this season.
Christian Eriksen has also proved himself to be a quality playmaker, and for as long as Hugo Lloris and Jan Vertonghen remain at the club, Spurs will have the spine of a very decent side.
Let’s hope the summer spending is good, and not in the same style as it was when some of these shockers were brought to White Hart Lane in the past.
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Click on Mauricio Pochettino to reveal the worst Tottenham XI of all time
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Heurelho Gomes
Looking back, Tottenham were to eager to dispose of Paul Robinson after the former England goalkeeper endured a difficult 2007/08 season.
However, the £10 million signing of replacement Heurelho Gomes can only be described as a disaster!
The Brazilian goalkeeper was signed on his reputation of having been a Champions League goalkeeper with PSV Eindhoven but his catalogue of howlers at White Hart Lane meant he was swiftly replaced as number one.
He now finds himself at Championship outfit Watford.
Pascal Chimbonda
The Frenchman enjoyed a decent season with newly promoted Wigan, and then had the cheek to hand in a transfer request whilst still in his kit following the final game of the season.
His attitude then didn’t serve as a warning for Tottenham, who signed him in the hope he would recreate some of the fine moments he did during his debut season in England.
Chimbonda looked way out of his depth, and his performances would go on to prove he should be considered nothing more than a one season wonder – and an average one at that.
Calum Davenport
Signed in the summer of 2004, Tottenham thought they were getting a future England centre back to partner Ledley King.
Yet Calum Davenport was simply not good enough during his time at White Hart Lane.
He managed just 15 league appearances, and was shipped out on loan three times before eventually making a permanent switch to West Ham in 2007 – where he was even less successful.
Anthony Gardner
Signed from Port Vale in 2000, Gardner was another ‘future England star’ Tottenham thought they were getting their hands on.
In eight years at White Hart Lane, Gardner was unfortunate with the injuries he suffered, and the way in which he could never force his way into the first team for an extended period of time.
To sum it up, Gardner played under seven managers at White Hart Lane before his eventual transfer to Hull – and he wasn’t a first choice under a single one.
Lee Young-Pyo
Signed in 2005 by Martin Jol, the Dutchman described his new addition as ‘the best left back in Holland.’
The Dutch league has never really been a good way to measure talent when it comes to signing for a Premier League club, and the South Korean international proved no exception.
After a quietly impressive start, Lee faded badly during a season in which Tottenham managed a disappointing 11th placed finish.
He moved on to Borussia Dortmund, where he only managed one season.
Andy Reid
Brought in from Nottingham Forrest on January transfer deadline day 2005, Reid was considered an exciting young winger capable of making the move up to the Premier League.
Despite a promising start at White Hart Lane he struggled to reproduce the form he had shown at Forest.
Making only 20 starts in his 26 appearances and netting just one goal for Spurs, he has to regarded as a terrible signing.
He was sold to Charlton Atheltic in 2006 and Spurs fans quickly forgot about him.
Michael Brown
Another player signed from the division below that simply couldn’t cut it at White Hart Lane.
Michael Brown will be remembered as one of the dirtiest (and worst) midfielders to play for Tottenham, as he made little to no impact following his arrival from Sheffield United in 2004.
He managed just two seasons in north London, before making the switch to London rivals Fulham. He has since gone on to play for another four clubs, and can currently be found at Port Vale.
Sean Davis
The midfielder arrived at the same time as Michael Brown (the summer of 2004) and stayed for the same amount of time, somehow managing to make even less of an impact.
Davis has been an impressive part of the Fulham side that had established themselves as a Premier League side for two years previously, yet he looked completely out of his depth at White Hart Lane.
He left for Portsmouth in 2006, having managed just 15 Premier League appearances for Spurs.
David Bentley
Tottenham brought into the David Bentley hype following a decent spell at Blackburn Rovers for the former Arsenal midfielder.
So much so in fact that they paid an incredible £15 million to sign him, probably in a rush to prevent others snapping up ‘the new David Beckham’.
Bentley was a major disappointment at White Hart Lane and has since had loan spells in the Championship and in Russia, before retiring from football at the age of 29, saying he had fallen out of love with the game.
Darren Bent
Tottenham supporters were thrilled with the £16million signing of Darren Bent in the summer of 2006, given his previous goal scoring record at Charlton.
Bent never settled at Tottenham however, famously missing a chance Harry Redknapp claimed ‘my missus would have scored.’
Bent moved to Sunderland, before Aston Villa paid a massive £24million for him in January 2011.
Based on his price and reputation before signing, Bent has to make this worst Tottenham XI – for similar reasons as his strike partner…
Roberto Soldado
£26 million of disappointment.
Soldado seems a nice enough bloke, but his Premier League goal record has been horrific since signing from Valencia – where of course he was scoring goals for fun.
The only current Tottenham player to make this list, we think it will be a miracle if he is still in north London next season.