Top 10 most expensive Tottenham signings ever: Two future legends mixed with disastrous flops

With Tottenham looking increasingly likely to smash their transfer record as they get fully behind boss Ange Postecoglou, TT decided to look at the club’s top 10 signings of all time.

Spurs have already been fairly active this summer, offloading some of the deadwood in Postecoglou’s squad and bring in Timo Werner on loan again along with the additions of hugely talented young midfield duo Lucas Bergvall and Archie Gray.

But more are expected to follow as Postecoglou targets a prolific No.9, almost certainly another central midfielder and most likely another centre-back to strengthen an area that proved problematic during the first half of last season.

The likes of Ivan Toney, Santiago Gimenez, Jonathan David and Viktor Gyokeres, although the latter is the only one of those names mentioned who would likely obliterate their current transfer record given his escape clause sits at £86m.

Eberechi Eze continues to be linked with a £60m switch to north London, although Manchester City well have stolen a march on Tottenham on that front.

However, the mere fact that Daniel Levy is seemingly now more than willing to splash out those sorts of figures to back a Tottenham manager who is already pushing the popularity of the Mauricio Pochettino era suggests that a record buy could well be around the corner.

10: Archie Gray £30m

The latest addition to the Tottenham ranks certainly comes with a big reputation after his outstanding efforts with Leeds United last season, which saw them just miss out on a quickfire Premier League return.

Gray, 18, has been signed by the club to play central midfield but the fact that he can also fill in at right-back is a massive added bonus for Spurs and Postecoglou.

Despite just being a teenager, Gray will be putting pressure on the likes of Yves Bissouma and Pape Sarr at the heart of Postecoglou’s engine room – especially if he excels in pre-season.

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9: Moussa Sissoko – £30m

There was a strong feeling when Sissoko arrived in north London that he was brought on the basis of how brilliantly he used to perform seemingly every time he played against Tottenham.

Spurs beat Everton to Sissoko’s signature in 2016 but he never reached the heights many had hoped for, despite the odd barn-storming display.

He spent five years at Tottenham before eventually joining Watford and after a two-year stint back in his homeland is now back playing at Vicarage Road.

8: Micky van de Ven – £34.5m

Without a shadow of a doubt one of the best Premier League signings of last season and an absolute masterstroke addition from the club when many were questioning bringing in a young Dutch bloke from the Bundesliga.

Speed to burn and a tremendous ability to read the game as well, Van de Ven also showed his ability as an attacking threat when he played at left-back for the last couple of games of the season.

The Dutchman, who did not really get the chance to showcase his talents at Euro 2024, should be a mainstay at the heart of Tottenham’s defence for the next five to six years.

7: Pedro Porro – £40m

Former Spurs boss Tim Sherwood’s initial diagnosis after Porro’s first start for Tottenham in a 4-1 mauling at Leicester was that he was ‘so bad it’s unbelievable’. But the Spaniard has come a long way since then.

Porro was outstanding last season, notching four goals and adding seven assists in 37 games in all competitions and has clearly shown that he belongs in the English top flight.

The 24-year-old will be the first-choice starter for Postecoglou again when the new campaign starts, despite talk of the addition of a new right-back after Japhet Tanganga’s exit and the likely sale of Emerson Royal.

6: James Maddison – £40m

A real season of two halves for the England playmaker in his first campaign in north London.

Maddison was sensational through the first 10 games of the season as Tottenham sat top of the table but, after an ankle injury ruled him out for over two months, he never returned to anything like those heights.

Indeed, his struggles led to a devastating axing from the England squad for Euro 2024.

However, Maddison is the sort of character who will come out swinging to prove people wrong so big things are expected of the 27-year-old ahead of the upcoming season.

5: Davinson Sanchez – £42m

Sanchez was the club’s record signing when the arrived from Ajax back in 2017 but ultimately disappointed after spending six years in north London.

The Colombian actually started his career at Tottenham strongly as he played in the middle of a back three with the ever-reliable Jan Vertonghen and Toby Alderweireld either side of him.

However, he was not as comfortable in a four and often looked uncomfortable and clumsy in possession.

It was no great surprise when he left for Galatasaray in September 2023, although that should have probably come much sooner given his lack of playing time over the previous few campaigns.

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4: Cristian Romero – £42m

Another terrific signing for what now looks a bargain fee and it’s hard to imagine that Romero actually cost the same as Sanchez!

Disciplinary issues aside, Romero has been a strong presence for Tottenham and has become a World Cup winner since moving to the club.

Hi partnership with Van de Ven could be a mainstay for years to come, if Levy and co. can keep him from out of the clutches of an envious Real Madrid.

3: Brennan Johnson – £47.5m

An Ange Postecoglou buy last summer who showed flashes of why the club forked out nearly £50m for his services without really ever hitting the heights that were probably hoped.

The Wales international has many of the qualities that should make him a dangerous winger in the Premier League but there was just a feeling that he was transitioning his way into playing for a bigger club.

Johnson will certainly need to his the new season running as competition for the wide berths in Postecoglou’s front three will be pretty fierce.

The former Forest man is currently competing with Dejan Kulusevski for a spot on the right but Manor Solomon will be back from injury and talk over a deal for Eberechi Eze remains.

2: Richarlison – £60m

A disastrous first season in north London was at least followed up by a much-improved effort from the sometimes-moody Brazilian last time around.

Richarlison looked more at home playing under Postecoglou than he did Antonio Conte, notching 12 goals in 31 games but rumours persist over a potential switch to the Saudi Pro League as Tottenham eye a more prolific No.9.

However, if that does not happen then expect the former Everton man to start the season centrally, with skipper Son Heung-min back in his favoured left-wing position.

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1: Tanguy Ndombele – £63m

Three words: Waste of money. Another three: Waste of talent.

Ndombele looked a rare talent when arrived in huge deal by Tottenham standards back in 2019 after the disappointment of the Champions League final loss to Liverpool.

In total he made just 91 appearances for the club, scoring 10 goals and was loaned out to Lyon, Napoli and Galatasaray.

The 27-year-old is now back in his homeland at Nice after being released from his Tottenham contract with one year left remaining.