Tottenham Hotspur have hardly enjoyed the most proficient transfer history, with a lengthy rogues gallery consisting of Daniel Levy's greatest failures during his tenure as chairman.

Although there were certainly many duds before he took over, it has only been the last two decades that saw truly astronomical fees began entering the game. First spurred on by Neymar's £200m move from Barcelona to Paris Saint-Germain, such a deal has made £100m+ moves commonplace, with north London rivals Arsenal spending £105m for Declan Rice, just weeks before Chelsea would spend £115m on Moises Caicedo.

Whilst the Lilywhites have never come close to unloading a figure anywhere near that level, there have been numerous high-profile blunders that have racked up a ridiculous amount of money wasted.

Pundit Noel Whelan would even note, back in 2021: "You’ve still got to pay to get Pochettino from PSG. You’re paying Mourinho his package for letting him go early. I mean, how much money do they really want to waste? Especially when they’ve got a fine for the breakaway to pay as well. It’s rattling up. This is taking away from their transfer budget. Now you’ve got to pay for him again.

“It just becomes a laughing stock at Tottenham, the amount of money they’ve wasted. He’s going to be coming into a Tottenham that’s not in the healthiest of positions.”

Whilst last summer marked a huge step in the right direction, it will take years to truly expunge the decades of failures that came beforehand.

Who is Spurs' most disappointing ever signing?

When it comes to the club's most disappointing ever deal, there are plenty to choose from.

Expectation is often high when a huge fee is spent, and with Tanguy Ndombele, that was no different. Joining for a club-record £63m fee, the Frenchman is the closest Levy has ever come to spending near to the Rice or Caicedo figures.

Having shone in Lyon, with his skilful, attractive play style set to capture the imagination, it did not take long for such a huge price tag to weigh on the shoulders of the midfielder, who would fail to meet the impossible standards set. He has since featured 91 times, scoring just ten goals having recently been exiled to his third loan spell.

Another example marks a more recent disappointment, as Richarlison still has just two Premier League goals for Spurs since making his £60m move back in 2022. The hope is that Postecoglou can start to usher out some form from the Brazilian, who will be desperate to start paying back such an investment.

Whilst on the topic of misfiring strikers, harking back to 2007 noted their acquisition of Darren Bent, who was poised to spearhead an exciting new period in north London after he had looked electric up front for Charlton Athletic.

Having scored 37 times in 79 games for the Addicks, it was largely expected that, alongside a higher calibre of teammates, the Englishman might take his goalscoring to elite heights.

However, it proved a troublesome two years for the 39-year-old, who now works for talkSPORT as a pundit.

2009/10 (Sunderland)

38

24

4

2008/09 (Tottenham Hotspur)

33

12

2

2007/08 (Tottenham Hotspur)

27

6

5

2006/07 (Charlton Athletic)

32

13

1

2005/06 (Charlton Athletic)

36

18

1

The 12-cap finisher would only score 25 times across another 79 appearances before departing for Sunderland in a hurry. Despite threatening to reignite his career with the Lilywhites under Harry Redknapp, the damage had already been done under Juande Ramos.

Wearside would be his next destination, where he enjoyed a truly prolific spell to exacerbate Levy's failures in the market once again.

How much did Darren Bent cost Spurs?

After such blistering form down south which could not halt their eventual relegation, it marked what seemed like a fine opportunity in the market for Levy to swoop.

As someone renowned for his frugality, and a well-documented lover of a good deal, it made little sense that he was so willing to part with a whopping £16.5m fee, becoming the club's record signing.

Martin Jol had talked up such a huge acquisition at the time, noting: "He has pace, he links play well and can see a pass – he can exploit the space and play as well. He knows Spurs is the place to be and that's something to be proud of."

What was Darren Bent's salary at Spurs?

Such a huge fee was always bound to warrant an equally impressive contract, and given his youth and inexperience, that was surprisingly exactly what he got.

In fact, it was The Guardian that revealed his £40k-per-week salary, when detailing the £80k fine he had received in 2009 for "inappropriate" Twitter posts.

This came as the striker sought to lambast the club's chairman, sending one final dig before that eventual move to Sunderland. He would tell Levy to "stop f***ing around", claiming: "It's so frustrating. Seriously getting p***ed off now," as he awaited the completion of the deal.

To add the £4.16m spent on his wages to that £16.5m transfer fee, and in total the forward would cost £20.66m. Therefore, for every goal he scored whilst at Tottenham, the club had to fork out £800k.

What did Darren Bent say about his time with Spurs?

Bent has been very open since becoming a pundit, speaking at length about a fine career that saw him score goals wherever he went.

However, it was only in 2009 that he revealed all on that ill-fated move to N17, strongly criticising his former manager in Redknapp alongside the culture of the club: "It was the worst two years of my career. Even last year, when I was the club's top scorer, I never actually felt wanted. I didn't feel Redknapp wanted me there. It's massive to have the support of your manager and that's not been the case for the last two years.

"My career stood still at Tottenham. There's a lot of politics going on there. I scored a lot of goals but it was the hardest two years of my life and it's a weight off my shoulders that I'm finally here. I never felt I would stay in the team even when I was scoring goals."

The former England international would end his scathing rant by suggesting that "Sunderland have the potential to go beyond Spurs."

Unsurprisingly, this was a notion unfulfilled, but not without Bent's fierce attempts to do so. He would enjoy arguably the outstanding year of his career at the Stadium of Light, scoring 24 in the Premier League across the 2009/10 season – a major improvement on the dross he served up at White Hart Lane.