Planet Football

While Daniel Levy had a reputation for being a thrifty spender during his tenure as chairman of Tottenham Hotspur, he was not always so averse to getting his chequebook out.

With more than £1.5 billion spent during his nearly 25-year tenure, there have been some hits but also plenty of misses along the way, so we are taking a look at his top 10 most expensive purchases.

To make things fair, we have left out signings made this summer so while Mohammed Kudus has made a promising start to his Spurs career, he does not feature in the list. Club record signing Xavi Simons is also absent having not yet kicked a ball.

Here then are Levy’s top 10 most expensive signings ranked:

In July 2019, Spurs broke the bank to bring midfielder Ndombele to north London from Lyon, but the French footballer never repaid them.

Arguably one of the most naturally talented players on this list, he was also one of the laziest with Jose Mourinho in particular feeling frustrated by his lack of work ethic.

Mourinho was more than happy to hang the player out to dry after a poor showing and the Portuguese Special One was not the only manager to fail to get the best out of him.

In the end, Spurs sent him on a series of loans before mutually terminating his contract in 2024.

Ninteen goals in the 2023-24 season with Bournemouth was convincing enough for Tottenham to part with £65million, but Levy and co. were perhaps blinded by that stellar year rather than taking a wider look at his whole career.

The striker has never been prolific and before his final campaign with the Cherries, he had never scored more than six goals in a Premier League season.

As Spurs have found out, he has also had plenty of issues with injuries. His first season in north London saw him miss 14 games and he is currently out with an ankle knock.

Another player blighted by injury has been Maddison, who has shown moments of excellence but those moments have been few and far between.

A promising career with Norwich earned him his move to Leicester, where he developed into one of the best No.10s in the Premier League.

But 24 games missed in his first season, coupled with a season-ending cruciate ligament tear this campaign, mean that Spurs haven’t seen much value for money for the £40million they paid for him in 2023.

Xavi Simons’ arrival may mean Maddison finds it hard to break back into the squad once he returns from injury.

Tipped by manager Pochettino to be one of the best centre-backs in the league, Sanchez never really lived up to the hype he earned at Ajax.

The Colombian had a promising start but faded away, and a costly own goal in a 3-3 draw with West Ham in October 2020 highlighted his struggles.

To his credit, he had a mini-form revival but was largely made a squad player and left for Galatasaray in 2023.

In the four seasons Richarlison was with Everton, he only once scored less than 10 goals. At Spurs, he has failed to hit that tally in two of his three seasons so far.

There’s talent there undoubtedly, but he is a player who goes through hot and cold spells and last campaign he managed just four goals in 15 league matches.

He has started this season much better, scoring twice in Spurs’ three games so far, but the question with Richarlison always is – how long will this last?

Spurs forked out £60million for the Brazilian in 2022, but he has yet to deliver anything close to what is expected of that price tag.

We are still very much in the ‘wait and see’ part of Gray’s Spurs career as the teenager has yet to make a meaningful mark on the team.

His first season saw plenty of game time with a total of 46 matches across all competitions, but he was shifted about the pitch a lot.

The calamity that was Ange Postecoglou’s final Spurs season is perhaps not the best breeding ground for youngsters.

Thomas Frank appears to back him though, starting him in midfield for Spurs’ first league game of the season, but there is still a long way to go in his career.

Solid if not overly spectacular, is probably the best way to describe Porro at Spurs.

He was an Antonio Conte signing, having joined from Sporting in the 2023 winter window, but has survived numerous manager changes to still be part of the squad.

Now under Frank, the full-back has played in all three games so far and is Spurs’ best right back.

The early signs of this season would suggest Johnson is ready for his breakthrough season in north London.

The winger arrived with plenty of hype, having left boyhood club Nottingham Forest to join Spurs in 2023 for a fee of £47.5million, but he managed just five goals in his first season.

The following year saw an improvement of that figure up to 11 and he was arguably one of the better players in Postecoglou’s dysfunctional side.

But this year, he has already scored two goals in three games and looks ready to become one of the better wingers in the Premier League.

QUIZ: Can you name every Tottenham manager of the Daniel Levy era?

The Argentinian may have more than one moment of madness in his locker.

But, when he’s not throwing his body into reckless tackles, the ‘absolutely mad’ defender as Gary Neville once described him has been a stalwart for Spurs for four seasons.

The first game of this season saw him notch up his 100th Premier League appearance and reports he could be off to Atletico Madrid ended up being shot down, such is his importance to the Spurs squad.

An undeniable hit is Van de Ven, who has become one of the best centre-backs in the league and one blessed with natural talents.

A rare mix of being nearly two metres tall but also lightning quick, the centre half is still only 24 but has already made himself an integral part of the north London team.

He has played every minute of Spurs’ league campaign so far and if he continues on the same trajectory, it is not hard to see some of Europe’s top clubs come calling.

READ NEXT: 15 of the funniest internet reactions to Daniel Levy stepping down at Tottenham

Tottenham Hotspur churned through 20 managers during the Daniel Levy era – but how many of them can you remember?

Levy oversaw 15 different managers and five interims during his time as Spurs chairman, with wildly different results.

We’re asking you to name as many as you can in just 10 minutes. The clue is the year (or years) of their managerial reign, and a temporary manager is also indicated.

If this puts you in the mood for more Spurs-related trivia, then have a go at naming the Lilywhites’ top 30 goalscorers of the Premier League era.

If you enjoy our quizzes, head to our new Football Games home where you can search an archive of over 1,000 quizzes and play them all in beautiful full-screen mode.

Good luck and don’t forget to tweet us your scores @planetfutebol.

Daniel Levy has stepped down as executive chairman of Tottenham Hotspur after almost 25 years in the role – and the club’s fans have celebrated the news on social media in hilarious ways.

Levy will always be regarded as one of the most contentious figures in Tottenham’s history.

He was the driving force behind the club’s brilliant new stadium, which stands comparison with any in world football, to the ultra-modern training headquarters at Hotspur Way in Enfield.

But, for most supporters, Levy’s time at the top will always be overshadowed by the lack of success on the field. Spurs have won just the League Cup and Europa League since 2001, with several near-misses.

Mercifully free of AI slop but with some charming reaction videos and hubristic boasting thrown in, we’ve collated 15 of the funniest reactions and memes to the departure many Spurs fans have been awaiting for years.

READ NEXT: The jaw-dropping XI of stars Tottenham almost signed under Daniel Levy

From Willian to Eden Hazard, Tottenham supporters know the pain of seeing some top players choose to go to Chelsea over their club – but it’s not always one-way traffic – as the imminent signing of Xavi Simons demonstrates.

Simons was of strong interest to Chelsea earlier in the summer of 2025, but Tottenham swooped in at the last minute to convince the Netherlands international to move to north London instead.

Alongside Simons, we’ve identified five other players who reportedly chose Spurs over Chelsea.

Xavi Simons

We doubt Tottenham technical director Johan Lange reads our work here at Planet Football, but we want a consultancy fee if he does.

“Twelve years after the Willian hijacking… wouldn’t it feel extra sweet to get one over the Blues?”

That’s the question we asked when we stuck Simons’ name on the shortlist of potential James Maddison replacements. Well, Spurs fans – how does it feel?

At the time, Chelsea appeared in pole position to sign the talented Dutch playmaker from RB Leipzig.

But we suggested that Spurs should try to hijack the deal by offering him a more clearly-defined role in the starting XI. And so it’s proven the case.

He’s completed a medical and the clubs have agreed on a fee.

Given what happened with Willian, we understand any Tottenham supporters who won’t believe it until an official announcement – but it sounds like this one is done and dusted. Surely.

Danny Rose

“I started at Leeds when I was 11. I came to Tottenham at 16. When I joined Leeds I was pretty raw,” Rose reminisced on his early years in an interview with Instagram channel don.emusic.

“I didn’t know about one-touch passing. It took me a couple of years to get to grips with everything and by the time I was 14 I was one of the best.

“I could have gone to Chelsea when I was 15, I went to the training ground but I didn’t fancy it and I chose Tottenham the year after.

“It was pretty daunting, I was nervous, I needed it. You know what 15-year-olds do when they are around their mates all the time. I needed to get away and I am glad I did.”

That choice worked out alright for Spurs. After announcing himself with that unforgettable screamer in the North London Derby, he made over 200 appearances for the club and for a time was one of the best left-backs in the country.

Steven Pienaar

The South Africa international joined Spurs in a £3million deal back in January 2011, but Chelsea reportedly also agreed a fee with Everton. The choice was ultimately down to the player.

“It wasn’t about the money, it was about ambition,” Pienaar told The Guardian.

“We want to fight and to play every game at the highest level and play in the Champions League and that’s what I want every season, and that’s why I made the decision to join Spurs.

“The decision I made may not be the right one, but I followed my heart and prayed for the answer. Joining Tottenham was the answer.

“I asked a lot of people and some said go to Chelsea, some said go to Spain, some said go to Tottenham. Some may not like it but this is my decision. If I fail then it’s my responsibility.”

Unfortunately it didn’t really work out for Pienaar in North London, and after making only a handful of appearances in half a season, he returned to Everton.

Brennan Johnson

Chelsea were reportedly one of the leading clubs in the race for Johnson’s signature back in the summer of 2023.

That makes sense, given that they were still seemingly targeting every young wide attacker on the market in those early Todd Boehly years.

They lost out on Crystal Palace’s Michael Olise and ended up bolstering their attack with Christopher Nkunku, Nicolas Jackson and Cole Palmer during that window.

The Daily Mail claimed that Johnson preferred Spurs “over a bloated Chelsea side in order to get more game time.”

Mohammed Kudus

According to The Sun, Chelsea offered Kiernan Dewsbury-Hall plus a further £20million to sign the exciting Ghanaian dribble king from West Ham.

Kudus was high on the Blues’ list of targets, while the player was open to a move to Stamford Bridge – even going as far as agreeing personal terms.

Ultimately, Tottenham’s swift and decisive approach won out. Who knows how things might’ve turned out had they taken the same tack with Morgan Gibbs-White or James Maddison?

James Maddison

Chelsea spent somewhere in the region of £1billion over the course of Boehly’s first year at the helm and Leicester City playmaker James Maddison had frequently been cited as a top target in their potential rebuild.

Many reports suggested that Chelsea opted against Maddison due to their youth-focused recruitment strategy. They ended up signing 21-year-old Cole Palmer instead.

But that’s reportedly not entirely true. Maddison’s heart being set on Spurs was also a factor.

“Chelsea’s strategy has been to largely look at players 25 years old and under,” transfer reporter Ben Jacobs told Caught Offside.

“And it’s true they passed up on going for James Maddison, who is now 26. But that wasn’t really down to age alone.

“There will always be exceptions to the age ‘rule’. After all, Mauricio Pochettino is also very keen on having Premier League experience. That’s why Raheem Sterling is seen as so important this season.

“Chelsea looked at lots of targets, which is normal in a busy window. But they also knew Maddison preferred the move to Spurs.”

READ NEXT: Celebrating Chelsea, Tottenham & the 2016 Battle of the Bridge: ‘Most shameful game’

Arsenal have hijacked Tottenham‘s move for Crystal Palace playmaker Eberechi Eze, leaving Thomas Frank’s side in need of another player.

For the past week, Spurs have been the frontrunners to sign the 27-year-old and until yesterday, everything pointed towards Eze joining Tottenham.

However, following an injury to Kai Havertz, Arsenal have swooped in and have agreed personal terms with the England international.

With Tottenham’s move now dead in the water, we’ve identified five alternatives that they should target.

Xavi Simons

If Arsenal can hijack transfers, then so can Tottenham.

Chelsea have been heavily linked with Simons all summer and have been in discussions with RB Leipzig, although as of writing, no agreement has been made.

It’s thought that before committing to signing Simons, Chelsea are trying to offload some of their own players in order to balance the books.

The 22-year-old is keen to join Chelsea, but until a deal is struck with RB Leipzig, he won’t be able to make the move.

With Chelsea taking their time over the transfer, Tottenham could attempt to hijack the deal themselves.

Simons is just the sort of player that Frank is after and, like Eze, is capable of playing in a number of different roles.

It seems like a long shot, but it’s a deal worth considering from a Tottenham perspective.

Mikkel Damsgaard

Frank is already familiar with Damsgaard and for that reason, a move for the Brentford playmaker cannot be ruled out.

The 25-year-old created 63 chances in the Premier League last season, the seventh most of any player in the league.

Of those 63 key passes, 10 of them were converted into assists, making Damsgaard statistically one of the most creative players in England.

Given the other players that Brentford have lost this summer, they’d likely drive a hard bargain when contemplating Damsgaard’s sale.

The Bees are also in a strong position to negotiate his price tag, given he’s under contract until 2030 with the option of an extra year.

Nonetheless, we think he’d be a great option for Spurs.

Nico Paz

Tottenham have also been linked with Como’s Paz, although Sky Sports have reported that this would be a ‘difficult deal’ to pull off.

The 20-year-old attacking midfielder impressed in Serie A last season, producing six goals and eight assists in 35 appearances.

It’s worth noting that Real Madrid do have the option to re-sign him for just €9million next summer, leading to speculation that he could return to Spain in 2026.

“You never know what the future holds,” Paz told reporters when asked about his future.

“I’m focused on Como, which is where I belong. I am very happy and excited. I have no idea what the future holds for me, I don’t even know what I’ll do tomorrow.”

Justin Kluivert

Spurs were keeping tabs on Kluivert earlier in the window and could resurface their interest after missing out on Eze.

The 26-year-old created 45 chances in the Premier League last season and produced an impressive 18 goal contributions for Bournemouth.

He’s still under contract until 2028, so wouldn’t come cheap, but he’s definitely an option worth exploring.

Maghnes Akliouche

Akliouche has been steadily improving year upon year and it’s no secret that Tottenham are interested.

The 23-year-old produced 19 goal contributions across all competitions for Monaco last season, predominantly playing on the right-hand side.

However, Spurs aren’t alone in their interest as PSG and Manchester City have also been linked with the Monaco star in recent weeks.

Reportedly valued at £60million, a bidding war could take place in next couple of weeks.

READ NEXT: The 7 Son Heung-min alternatives Tottenham considered in 2015 & how they’ve fared

Arsenal‘s hijack to beat Tottenham to the signing of Eberechi Eze was an all-timer of a day on social media for phone-addicted football fans everywhere.

Instantly up there with Samir Nasri’s trip to the Drip Doctors, the backlash to the European Super League, or for old-timers Mesut Ozil’s 2013 signing from Real Madrid… Eze’s transfer bombshell sits alongside with the best of them.

We’ve rounded up some of the best reactions from Twitter/X for your viewing pleasure, mercifully free of any AI slop or dodgy Romano photoshops.

Before the news

Tottenham fans

Arsenal fans

READ NEXT: Ranking the 10 biggest transfer hijackings of all time: Eze, Gascoigne, Keane…

Arsenal have hijacked Tottenham’s bid to sign Eberechi Eze, getting one over their north London rivals who appeared in pole position to sign the Crystal Palace and England star.

It appears increasingly certain that Arsenal will pull off something of a coup in signing Eze, long established as a potential difference-maker for an elite club.

Here are five of the most notable names who opted for Arsenal over Spurs – and the stories behind their choices.

William Saliba

Saliba revealed that playing for ‘the biggest club in England’ led to him choosing the Gunners over local rivals Tottenham back in 2019.

Speaking to Arsenal’s official website, the teenager insisted he only had one club in mind, adding: “Since I was little, I’ve been watching Arsenal play in the Champions League and so on.

“It’s a massive pleasure to sign for a really, really big English club. This is the biggest club in England for me, so it was an easy decision.”

Arsenal were struggling under Unai Emery at the time, while Spurs had just reached the Champions League final, making Saliba’s statement especially bold.

But he’s become one of the Premier League’s best defenders as Arsenal have revived under Mikel Arteta, while Tottenham have usually fluctuated a few places below them.

David Raya

This is certainly an interesting example of one who got away from Spurs back in 2023.

After being told it was £40million or no deal by Brentford, Raya was then able to leave to join Arsenal for a fee of around £27million.

A frustrating deal for multiple reasons, losing a player of his quality to their North London rivals hurt and it was made all the worse given how Guglielmo Vicario has struggled with injuries across his time at the club.

Riccardo Calafiori

After helping Bologna reach the Champions League and enjoying a stellar Euro 2024, Calafiori was on the shopping list of several Premier League clubs.

Chelsea, Newcastle and Tottenham all wanted the Italian defender, but he rejected them all in favour of a move to Arsenal.

Emmanuel Petit

Arsenal legend Petit once had Tottenham convinced he was going to sign for them – before he got into a taxi they paid for and went on his way to join their bitter rivals instead.

Eager to challenge for titles rather than fighting relegation battles, the future World Cup winner signed a £3.5million deal with the Gunners.

Speaking on talkSPORT, Petit explained: “I had meetings on the same day with Tottenham and Arsenal and had a meeting with Tottenham in the morning, but when I came to England I didn’t know about the rivalry between the two clubs.

“When I left the Spurs stadium, they booked me a cab and the cab driver asked me for directions, so I gave him the Arsenal address and I didn’t realise that the cab was pre-paid by Spurs, so they knew where I was going!

“I’d told Spurs that I needed time to think about it but knew that I had to see Arsenal, as well as other clubs in Italy and Spain.

“I told everyone that I’d make my mind up and when I knew the answer I would give it, but after a couple of days I signed for Arsenal and it went into newspapers and all of a sudden the story came.

“I realised the pressure of the rivalry then.”

READ: Remembering Emmanuel Petit’s incredible debut season at Arsenal

Reiss Nelson

Nelson admitted he could have joined Spurs’ academy as a youngster, but it was not a hard decision for the boyhood Arsenal fan to turn them down.

“I was nine years old, I used to play for a team in Catford,” Nelson told the Arsenal Weekly Podcast in 2017.

“I would get up every morning with my brother, get on the train and travel to Catford three times a week.

“I was there for about two months playing for a team called Moonshot FC. I got scouted for Tottenham and was there for three to four weeks before a phone call from Arsenal came.

“The first session they wanted to sign me so, happy days, I didn’t look back.”

Nelson has scored eight goals in 90 Arsenal appearances and is currently on loan at Fulham.

READ NEXT: Ranking every Arsenal signing under Mikel Arteta from worst to best

Tottenham Hotspur are in pole position to sign Eberechi Eze, getting one over their north London rivals Arsenal who have reportedly targeted the Crystal Palace star for a long time.

It’s not (yet) confirmed, but it appears increasingly certain that Spurs will pull off something of a coup in signing Eze, long established as a potential difference-maker for an elite club. He wouldn’t be the first.

Here are six of the most notable names who opted for Tottenham over the Gunners – and the stories behind their choices.

Stephen Carr

Academy graduate Carr made over 250 first-team appearances for his boyhood club, but he could’ve chosen Arsenal’s Hale End academy as a youngster instead.

“When I joined, I had the choice to play for Spurs or Arsenal, but I just felt Spurs was very homely,” reminisced the former Spurs stalwart in an interview with The Spurs Web.

“At that time, the training ground at Mill Hill wasn’t as fancy as Arsenal’s training ground, but I just found it more real. I ended up staying for 12 years and I loved every minute of it.

“I was around a squad that had a lot of managers come and go at Tottenham but the fans were unbelievable. We had a quality stadium, too.

“Obviously, now it’s a completely different level, it’s gone ridiculous, but it just felt homely for me. I felt at home coming from Dublin, I just felt the transition was quite easy.”

Richarlison

Mikel Arteta’s Gunners made an approach to sign Richarlison during the summer of 2022, when he was one of the most highly-rated strikers outside the Premier League’s traditional ‘big six’.

But Spurs, who pipped their rivals to Champions League qualification that year, acted more decisively to get a deal over the line.

“I know Chelsea made an offer, and I believe Arsenal also contacted Everton to ask about my situation, but Spurs came in and paid the fee, you know? It’s as simple as that,” Richarlison told reporters in Brazil, shortly after signing for Spurs.

“Everton had to sell some players to avoid a Financial Fair Play problem, and the negotiations were very brief, to be honest.

“I was on holiday in Brazil when I heard that Tottenham had made Everton an offer. I was happy because they are a huge team.

“Then it was all about the clubs negotiating a deal, and fortunately, everything went well.

“Antonio Conte called me during the negotiations and expressed how much he’d like to have me on board – that was vital for my decision.”

Arsenal instead signed Richarlison’s Selecao team-mate – and rival for the starting spot up top – Gabriel Jesus.

The two Brazilians have shown flashes of brilliance but ultimately struggled for form and fitness at their respective clubs.

You’d have to say that Richarlison looks the likelier to make an impact in 2025-26, given his eye-catching brace against Burnley and Jesus’ long-term ACL woe.

Benoit Assou-Ekkoto

Assou-Ekotto gives by far the best answer for choosing Spurs over Arsenal.

“Do you know why I didn’t sign for Arsenal?” Assou-Ekotto revealed years later.

“I asked my agent: ‘Do they go to the hotel before matches? He said yes, they do. I said I’m not going there. I want to have a life, not live in a hotel.’

“Then he told me that Tottenham didn’t do that, so I said ‘Cool, we’ll go to Tottenham!’

“What’s more, Arsenal were playing in the European Cup, which meant you weren’t at home four days a week!”

Remarkably on brand for a footballer who was famously not at all arsed about football. Never change, Benoit.

Jan Vertonghen

Vertonghen had talks with Arsene Wenger before deciding that Tottenham offered a better fit for how he saw his own strengths.

“Arsenal was also concrete, but they wanted to make me a midfield controller, an Emmanuel Petit type,” Vertonghen told Dutch outlet NU.

“I’m not afraid of competition, but the overall picture of Spurs appealed to me more.”

The Belgian signed for Tottenham in 2012 and made over 300 appearances over an eight-year spell. He proved himself one of the club’s best centre-backs of the Premier League era.

Probably a good thing he wasn’t thrown into Arsenal’s ailing midfield engine room in Wenger’s latter years, then.

Clinton Njie

Cameroonian winger Njie never quite lived up to expectations, but he was coveted by top clubs across Europe a decade ago after breaking through at Lyon.

He chose Spurs in large part due to Mauricio Pochettino’s impressive track record for developing young talent.

“I was never scared that my transfer to Tottenham would not be confirmed,” Njie told French paper L’Equipe.

“I never spoke to Arsenal representatives on the phone, they simply contacted my agent. My choice was made, I was determined to join Tottenham.

“Here, I will be working under Mauricio Pochettino, a manager who plays youngsters and allows them to progress.”

Unfortunately, it never quite worked out for Njie at Spurs and he won’t go down as one of Pochettino’s success stories. He only made a handful of appearances before returning to France with Marseille.

The 32-year-old is currently without a club and was last seen turning out in Romania for Rapid Bucuresti.

Emerson Royal

Sky Sports reporter Kaveh Solhekol revealed that Arsenal were interested in the Brazilian full-back, but his heart was set on a move to Spurs in 2021.

Spanish outlet Mundo Deportivo later corroborated those reports.

Fair to say, Mikel Arteta might consider this one a bullet dodged given how Emerson flattered to deceive for their rivals. Nowadays he’s back in Brazil, turning out for Flamengo.

READ NEXT: Where are they now? The Tottenham XI from Son Heung-min’s debut in 2015

Tottenham Hotspur are looking concerningly light when it comes to midfield creativity after a serious injury suffered by James Maddison in pre-season and the failure to sign Morgan Gibbs-White.

Maddison was stretchered off in Spurs’ 1-1 friendly draw with Newcastle United in South Korea, leaving Thomas Frank with a major headache ahead of the fast-approaching 2025-26 campaign.

It looks as though the club will have to spend some money to address the issue and we’ve identified six creative midfielders for Tottenham to target in the transfer market.

Maghnes Akliouche

Monaco playmaker Akliouche just seems to get better every season and the time feels right for him to leave his boyhood club to take on a new challenge elsewhere.

A first senior France cap is surely only a matter of time for the 23-year-old, given he was one of the best midfielders in Ligue 1 last term.

He notched five goals and 10 assists for Monaco as they achieved a third-place finish.

Akliouche has shone at various youth levels for Les Bleus and was part of Thierry Henry’s Under-23s that won silver at the 2024 Olympics. The kid has a very bright future.

Xavi Simons

It feels wild that Simons is still only 22 years of age, given he’s been established in Europe for a good while now – after making a name for himself as one to watch at La Masia a decade ago.

As is always the case with such immensely talented prospects, you can’t escape the sense that RB Leipzig is only a stop-gap before bigger and better things.

Chelsea lead the race for the Netherlands international’s signature, but it’s difficult to see exactly where he’d factor in alongside Cole Palmer and their bounty of attacking and creative options.

Tottenham, on the other hand, can offer Simons a clearly defined place in Frank’s first-choice XI – as well as Champions League football.

Twelve years after the Willian hijacking… wouldn’t it feel extra sweet to get one over the Blues?

Mikkel Damsgaard

Frank loves linking up with his Danish compatriots, while Spurs’ reported ill-fated pursuit of Bryan Mbeumo suggests he has no qualms over raiding his old club.

Damsgaard took his time to settle into English football, but he was an absolute revelation last season.

He notched double figures for assists and was constantly creating good goalscoring opportunities for Mbeumo and Yoane Wissa.

Like Maddison, he’s nominally a No.10 but fluid in his movements and position, dropping out wide to drag centre-backs out of position as well as deeper to contribute to build-up.

Brentford can’t afford to lose yet another key player, but from Tottenham’s perspective this would be a no-brainer.

Kamory Doumbia

It’s only been one season since Doumbia moved permanently from Reims to Brest, but the 22-year-old Malian already looks ready for the next step in his career.

He didn’t look out of his depth in the Champions League last season and looks as though he belongs at that level, but Brest failed to land any European football for the upcoming campaign after finishing midtable.

Doumbia’s name has been conspicuously absent from the transfer gossip columns this summer, but we’d be amazed if he doesn’t get a big move in a year or two.

Nico Paz

Outstanding as Cesc Fabregas’ newly-promoted Como punched above their weight to finish in the top half in Serie A last term, it’ll be interesting to see what the immediate future holds for 20-year-old wonderkid Paz.

Former club Real Madrid opted against exercising their staggeringly cheap buyback clause after signing fellow Argentinian wonderkid Franco Mastantuono, although it’s widely reported that they’ll still have the option next summer.

Dealing with Como might not be easy. They rebuffed Inter’s approach to poach Fabregas and given their ambitions, you imagine they’d fight just as hard to keep their star player.

But there could be a unique market opportunity there and Spurs would be daft not to at least ask the question.

Nadiem Amiri

According to FBref’s complex statistical algorithm, the player who is most similar in profile to Maddison over the past 365 days is… Arsenal captain Martin Odegaard.

Ahem. Let’s move on.

Second on that list is Mainz’s Amiri. At 28, the Germany international wouldn’t represent an investment with great resale value, but he’s at the peak of his powers and looks ready to make an instant impact.

Amiri made the 2024-25 Bundesliga Team of the Season and was probably Mainz’s standout player as they pushed for Champions League qualification.

READ NEXT: Where are they now? The Tottenham XI from Son Heung-min’s debut in 2015

Son Heung-min is one of the biggest legends in Tottenham Hotspur‘s history – but his debut for the club in 2015 wasn’t exactly the most memorable.

Signed from Bayer Leverkusen, Son made his first Spurs appearance in a 1-0 win over Sunderland and was substituted after 62 minutes.

Happily, things soon picked up for the South Korean forward afterwards. But what became of his team-mates from that September afternoon in the North East?

GK: Hugo Lloris

Lloris left Tottenham after 11 years and almost 450 appearances in December 2023, having fallen behind Guglielmo Vicario in the pecking order following the appointment of Ange Postecoglou.

“I needed something new, something different,” the former France captain explained on his decision to join MLS outfit LAFC.

“I had great moments in Europe. I was just looking for different opportunities, to experience a new continent, to experience a new life as well.”

The veteran goalkeeper has been a near ever-present between the sticks for LAFC in both of the last two MLS campaigns.

RB: Kyle Walker

Walker had already been at Spurs for four seasons by 2015 and had gradually become England’s starting right-back too.

Devastatingly quick, the Sheffield-born defender was eventually sold to Manchester City for £50million two years later and became one of the most successful players in Premier League history.

Now firmly in the autumn of his career, Walker has signed for Burnley and still remains part of the England squad.

CB: Toby Alderweireld

Alderweireld’s move to Tottenham caused plenty of controversy in 2015.

Southampton thought they had first refusal on the player after an impressive loan spell during the 2014-15 season.

But parent club Atletico Madrid cancelled that option and accepted a higher bid from Spurs.

It’s fair to say Alderweireld repaid the faith shown in him, making 236 appearances for Tottenham and becoming an essential part of their progress in the latter half of the 2010s.

He moved to Qatari side Al-Duhail in the summer of 2021, bringing an end to six years at Spurs, before ending his career back in Belgium with Royal Antwerp.

CB: Jan Vertonghen

The other half of Spurs’ excellent Belgian defensive duo, Vertonghen has also recently retired.

After spending a couple of years with Benfica, he ended his career at Anderlecht and played his final match in May 2025.

LB: Ben Davies

One of two players to join Spurs from Swansea in the summer of 2014, Davies arrived in a swap deal for Icelandic midfielder Gylfi Sigurdsson.

A highly-rated 21-year-old left-back, Davies remains at Spurs and has played over 350 games for the club.

The Wales international has come in for criticism at times, but, now 32, he is one of the more experienced members of the current squad and has overall been an excellent signing.

CM: Eric Dier

After almost 10 years of service and well over 300 appearances, Dier departed Tottenham in January 2024 to take on a new challenge at Bayern Munich.

An initial loan spell was enough to convince Bayern to sign the defender permanently and Dier became a surprisingly regular part of Vincent Kompany’s team.

He left the Bundesliga champions at the end of the 2024-25 season and signed for Monaco.

CM: Ryan Mason (Tom Carroll 85′)

A sad story with a happy twist. Mason left his boyhood club in 2016 to join Hull City only to be forced to retire two years later at the age of just 26 due to a fractured skull suffered in a clash of heads with Gary Cahill in 2017.

In April 2018, Mason returned to Tottenham on a voluntary basis to help coach youth teams while taking his coaching badges.

He became interim manager at Spurs on two separate occasions and is now head coach at West Bromwich Albion.

A promising young midfielder, Carroll ultimately became a perennial loanee at White Hart Lane, spending time at Leyton Orient, Derby County, QPR and Swansea City while making just 27 league appearances for his parent club.

The former England Under-21 international eventually left on a permanent deal, returning to Swansea in 2017.

After several unfulfilling moves, most recently to Reading for the second half of 2024-25, Carroll is now a free agent.

QUIZ: Can you name Tottenham’s most expensive signing from every year since 2000?

RW: Son Heung-min (Andros Townsend 62′)

Son will go down as one of the best signings in Tottenham’s history.

The South Korea international was purchased from Bayer Leverkusen for £22million 10 years ago and has since scored 173 goals for the club, becoming an integral part of that sensational Pochettino team.

Furthermore, Son has become a Spurs icon for his infectious spirit and unwavering loyalty to the club. Even neutrals were pleased for the forward when he lifted the Europa League trophy in May 2025.

Townsend was loaned out nine times by Tottenham before eventually breaking into the first team as an inconsistent winger who occasionally scored wonder goals.

Since leaving Spurs, he spent time at Newcastle United, Crystal Palace and Everton as an inconsistent winger who occasionally scored wonder goals.

He now plays in Thailand for Kanchanaburi Power and is also a blossoming pundit, regularly appearing on co-commentary for ITV.

CAM: Dele Alli (Eric Lamela 65′)

At his peak under Mauricio Pochettino, Dele was a force to be reckoned with.

The 29-year-old was a natural goalscorer in his younger years as he scored 67 goals for Tottenham across 269 appearances.

But injuries and off-field problems meant the attacking midfielder gradually slid from view. He’s now in Italy with Como, but is rumoured to be considering retirement after failing to rediscover his mojo.

Lamela was the last man standing from the seven players that arrived at Spurs in 2013, finally joining Sevilla in 2021 in a swap deal that saw Bryan Gil move in the opposite direction.

The Argentine winger was signed as a like-for-like replacement for Bale and was the most expensive of the seven arrivals that summer, costing £30million from Roma.

Lamela was plagued by a string of injury problems but did provide flashes of genius when fit, including not one but two rabona goals.

He now plays in Greece for AEK Athens.

LW: Nacer Chadli

Chadli signed from FC Twente for £7million and was a regular during his three seasons at the Lane, scoring 25 goals for the club including an impressive 13 in his second season.

The winger is one of two players on this list who Spurs actually made a profit on as they sold him to West Brom for £13million in 2015.

After two years at The Hawthorns, he had brief spells at Monaco, Anderlecht, Westerlo and Istanbul Basaksehir. At 36, he is now back in Belgium with Standard Liege.

ST: Harry Kane

Kane was going through a mini goal drought in September 2015, leaving some pundits to declare his breakthrough 2014-15 campaign was a one-off.

Now Spurs and England’s record goalscorer, Kane is tearing up at Bayern Munich and is considered one of the best strikers of his generation.