The Spurs Web

Amidst reports that Tottenham Hotspur could soon tie up a naming rights deal, Everton’s former chief Keith Wyness has made an interesting claim about Daniel Levy’s intentions.

Spurs in talks with company over naming rights deal

It has been five and a half years since Spurs moved into the Tottenham Hotspur Stadium, but the club are yet to find a naming rights partner.

It emerged last week that the North London club have held conversations with German logistics company DHL about a potential naming rights deal.

The update claimed that the Lilywhites had also previously spoken to the likes of Amazon and Google, although the outcome of those talks are unknown.

Keith Wyness claims Daniel Levy wants a bumper deal

Wyness believes that the Tottenham chairman would be holding out for an agreement worth £25m per season with DHL.

The former Everton CEO suggested that the stadium’s location and the fact that it is a multi-use venue will appeal to the German logistics company, who would be willing to pay a premium.

Wyness told Football Insider: “DHL have got the budget. The number I believe Daniel Levy has been sticking out for is £25million. Can he get £15million? I’m sure he’s been offered that. Can he get £20million? Possibly, DHL could get there with bonuses.

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“The attraction for DHL is that it’s a multi-use stadium. There’s usage all through the year. Being in London is a crucial part of it as well. I think there’d be a deal if they could push their budget to £20 million plus bonuses.”

Tottenham will be happy to bide their time

One of the reasons Levy is seemingly not in a hurry to get a naming rights partner is that hosting high-profile events like the NFL and big concerts at a venue titled ‘Tottenham Hotspur Stadium’, is a huge plus to the club’s brand.

The Spurs chairman would thus be happy to wait to hold out for as long as needed to get the kind of figure that he has in mind.

The stage is set for an electrifying quarter-final clash in the Carabao Cup at the Tottenham Hotspur Stadium, where Tottenham Hotspur and Manchester United will lock horns. With both teams coming off the back of crucial victories, this midweek fixture promises to be one of the most captivating encounters of the round. Let’s find out how you can watch Tottenham vs Manchester United in Carabao Cup action.

How to watch Tottenham and Manchester United in Carabao Cup action

Tottenham Hotspur ended their five-game winless run in the Premier League in stunning fashion, demolishing Southampton with a resounding 5-0 victory.

Ange Postecoglou’s men delivered a commanding first-half performance, with James Maddison scoring twice and further goals coming from Dejan Kulusevski, Heung-min Son, and Pape Matar Sarr.

This emphatic display saw the likes of Djed Spence and Lucas Bergvall earn their first Premier League starts since joining the club, both turning in impressive performances.

Crucially, with the game effectively won by half-time, Postecoglou was able to rest key players, including Son, Maddison, and Spence, giving them valuable recovery time ahead of this Carabao Cup showdown. It’s this freshness, coupled with their resurgent form, that gives Spurs fans renewed optimism.

Manchester United, meanwhile, come into this fixture off the back of a dramatic derby-day victory against Manchester City.

Despite trailing for much of the game, United turned the contest on its head in the dying moments, with Amad Diallo winning a crucial penalty converted by Bruno Fernandes in the 88th minute, before Diallo himself scored the decisive goal in the 90th minute.

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This hard-fought win not only boosted their confidence but also highlighted their resilience and tactical adaptability under their new manager, Rúben Amorim.

When and where is the game?

The game will be hosted at the Tottenham Hotspur Stadium on Thursday, 19 December 2024, with an 8:00 pm UK time kick-off.

How to watch Tottenham vs Manchester United in Carabao Cup

The match will be available to watch on Sky Go UK NOW, SKY GO Extra, Sky Ultra HD, Sky Sports Main Event, Sky Sports Football, Sky Sports+, and BBC Radio 5 Live.

Tottenham Hotspur vs Manchester United team news

Tottenham have several absentees going into this fixture, with Wilson Odobert, Guglielmo Vicario, Mikey Moore, Cristian Romero, Micky van de Ven, Ben Davies, and Richarlison all sidelined due to injuries. Additionally, Rodrigo Bentancur remains unavailable as he continues to serve his seven-game suspension.

For Manchester United, Jonny Evans is set to miss this game due to a knock that will likely keep him out until late December.

Luke Shaw is also unavailable as he recovers from a hamstring injury, expected to see him return at the end of the month, while Mason Mount’s muscle injury will keep him out until early January.

The Spurs Web prediction

Predicting this match is no easy task, with both teams high after impressive victories. However, the depth of Manchester United’s squad gives them a slight edge in terms of fitness and available options, particularly with Tottenham missing key players in defence.

That said, Spurs have already defeated United earlier this season, and their ability to start games at a blistering pace could be the deciding factor. If they can find early goals, as they did against Southampton, they stand a strong chance of securing another famous win.

Given the high stakes of this cup tie and the attacking intent of both teams, an entertaining and closely contested game is expected. Ultimately, Spurs’ newfound confidence and tactical fluidity under Postecoglou might just see them edge it.

As Tottenham Hotspur continue to build under Ange Postecoglou, the club is already setting its sights on the future, with plans to bolster their defence by targeting a ‘strong and powerful’ Championship captain in 2025.

Spurs need a left-sided centre-back

Tottenham Hotspur are actively searching for a left-sided centre-back to add balance to their defence, a need that has been magnified in recent weeks.

Injuries to Cristian Romero, Ben Davies and Micky van de Ven have left Postecoglou with limited options, forcing him to field the versatile yet inexperienced Archie Gray as a centre-half in recent games.

While Davies is expected to return before New Year’s Day, the situation has exposed the club’s lack of depth in that position.

Tottenham’s interest in Pascal Struijk

Reports indicate that Tottenham Hotspur, along with Brighton & Hove Albion and Wolverhampton Wanderers, are closely monitoring Pascal Struijk, the Leeds United captain.

Struijk, a Belgian-born Dutch international, has become a key figure at Elland Road, earning plaudits for his commanding performances in the heart of defence.

TBRfootball have confirmed that Spurs are keen to add Struijk to their ranks in 2025, with Leeds United now working to tie the player down to a new contract.

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However, the success of those negotiations could hinge on Leeds’ ability to secure promotion back to the Premier League under manager Daniel Farke. Should Leeds fail in their bid, Tottenham may see an opportunity to swoop in and secure Struijk’s services.

Tottenham’s relationship with Leeds United

Tottenham Hotspur’s recent dealings with Leeds United suggest that a move for Struijk could be more straightforward than it might initially appear.

The two clubs have developed a strong working relationship in recent seasons, highlighted by the summer transfer of Archie Gray to North London for a significant £35 million fee.

In the same window, Joe Rodon moved to Leeds on a permanent deal, while Manor Solomon joined the Yorkshire club on loan.

This cooperation could provide Tottenham with a crucial edge in their pursuit of Struijk. While it is unlikely that Leeds would entertain a January exit for their captain, Spurs could find themselves in a favourable position come the summer of 2025, especially if Leeds remain in the Championship.

Football finance expert Stefan Borson offers his take on what kind of naming rights agreement Tottenham and Daniel Levy will want and on how close a deal is at the moment.

Spurs have held talks with several parties over naming rights deal

Tottenham are still searching for a naming rights partner, five-and-a-half years after the opening of their new stadium.

It has been widely reported that Daniel Levy and co have talked to a number of high-profile companies about a potential deal, including the likes of Google, Amazon and DHL.

It has also been suggested by some sources recently that with the Tottenham Hotspur Stadium now hosting an increasing number of non-football events, the naming rights of the venue would be even more lucrative.

Stefan Borson believes Spurs will bide their time

Borson has now claimed that Tottenham have been speaking to interested parties even before the opening of the new stadium.

The finance expert claims that Daniel Levy could hold out for a £25million-a-year deal across 20 years, but explained that an agreement does not appear to be close at the moment.

When asked about Tottenham’s search for a naming rights partner, Borson told Football Insider: “They have been trying for a very long time. The process to try and find a naming rights partner has probably been going on for something like six or seven years.

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“They will have been looking for a partner way before the stadium was built. You would think it’s worth £25million for maybe a 10 or 20-year deal, but they have not been able to find somebody to take it.

“I very much doubt they are in advanced-stage conversations with anybody at this stage. I’m sure they will have had some offers, but ultimately, it won’t have been enough.

“One company would have valued it at £10-15million and Spurs would have said ‘Look, it’s the first sponsor, we are not going to give it away for anything that we think is less than it’s worth’.”

Time is on Tottenham’s side

The Tottenham Hotspur Stadium is becoming an increasingly more high-profile venue with each passing year, which means that the value of the naming rights deal continues to grow.

Time is thus on the side of the Lilywhites, which is why they are in a hurry to agree on a deal unless the offer meets their demands.

Two different Paraguayan outlets are of the belief that one of the country’s best players – Omar Alderete – could be on his way to Tottenham Hotspur in January.

La Liga centre-back on Tottenham’s radar

It has been widely reported over the recent days that Spurs are prioritising reinforcing their backline in January, given the injuries that the North London club are dealing with in their defence.

With Cristian Romero, Ben Davies and Micky van de Ven now out injured, Ange Postecoglou‘s men will likely be scouring the market for a centre-back.

It turns out that one Getafe man, who has been consistent for club and country over the last few years, has now emerged on Tottenham’s radar.

Tottenham in negotiations over a deal for Omar Alderete

This update comes from Paraguayan outlets, including D10, who say that Spurs are now making advances towards Omar Alderete.

The Spanish side initially signed the defender on loan from Hertha Berlin in 2022 and made his stay permanent the following year, and he has been a mainstay in their backline ever since.

It is alleged that the defender’s performances have caught the attention of Spurs, who are said to be in negotiations to secure his services next month.

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The same information is also backed by another outlet from the South American country, Antena 2, who are confident that the Paraguay international is on his way to Spurs.

They state that the Getafe player ‘would be signed’ by Ange Postecoglou’s side during the upcoming transfer window.

This information is likely coming from the player’s entourage

The fact that this story has not been picked up by either English or Spanish outlets and is only being reported in Paraguay is telling.

That suggests that it has been fed to the press by the player’s agent, which is why we would have to be careful with taking it at face value.

As injuries strike Tottenham once again, Ange Postecgolou is forced to rely on squad players who would usually not be starting as many games. One Spurs defender has now been told that he isn’t up to the standard of Premier League football.

Injuries forced Tottenham’s hand against Chelsea

The disappointment after Tottenham’s 4-3 loss against Chelsea started to reach fever-pitch. Spurs’ early 2-0 lead made it seem as if the team’s fortunes were turning.

However, Cristian Romero, Micky van de Ven and Brennan Johnson were all forced to leave the field prematurely. Tottenham’s squad depth was already lessened due to the absence of Wilson Odobert, Richarlison, Ben Davies, Mikey Moore and Guglielmo Vicario. Spurs’ substitutions were all forced with little other means to affect the game from the sidelines, which eventually led to Tottenham’s resilience crumbling.

It seems as if each week, Tottenham have fewer players they can turn to and the ones who are available are seeing errors enter their game due to overuse and fatigue.

Radu Dragusin described as ‘not good enough’

Speaking to BBC Radio Five Live Football Daily Podcast, former midfielder Nigel Reo-Coker, has criticised Tottenham centre-back Radu Dragusin.

Reo-Coker said (Premier League Review): “Injuries are a part of football, yes. You question Romero and van de Ven starting whether they were fully fit enough to start, and you lose two of your centre-backs.

“As soon as Dragusin comes in, he’s starting to show now maybe that the Premier League is a bit too much for him.”

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At the start of the season, the expectation would have been that Dragusin would generally start in Europa League fixtures and other cup matches.

The fact he has played in over half of Tottenham’s Premier League games, often situated on the left or without either of the first-choice centre-backs, is symbolic of how injuries are affecting Spurs’ season.

If you are going to criticise Dragusin, it’s necessary to be specific

There is such little value in suggesting the Premier League is ‘too much’ for a player. There are legitimate arguments to suggest that Dragusin being in Spurs’ team might hinder them.

His ability in possession makes it harder for Tottenham to play effectively from the back and allows the opposition to mark teammates and press Dragusin harder.

That being said, when he is tasked with box defending, Dragusin is imperious for a 22-year-old. He reads danger well and plays out bravely even while under pressure. Additionally, he looks far better when paired with a left-footed partner next to him (particularly Van de Ven).

There is little to suggest that playing in the Premier League as a whole is beyond his capabilities. Unfortunately, Tottenham’s tactical set-up does expose his weaknesses more than highlights his strengths. However, he is an extremely talented player and would fit in perfectly to any side that required a little less from their centre-backs in build-up.

Jamie Carragher may have hit the headlines for calling for Daniel Levy to step down this week but this was not the first time that the former Liverpool man has called out the Tottenham hierarchy.

The guns being pointed at Daniel Levy

It will delight some Spurs fans to see that on this occasion, Ange Postecoglou is not the only one bearing the brunt of the criticism for Tottenham’s poor displays this season.

Levy is also coming under a lot of scrutiny, with many feeling that the Tottenham chairman has failed to back yet another manager.

Popular media figures are now joining in the criticism, including Carragher, who said after Spurs’ loss to Chelsea on Sunday about the Spurs chairman: “It’s probably time for someone else to come in because to not win a trophy in that period of time with the managers they have had.

“They’ve not really ever gone out of their way in the transfer market, they’ve spent decent money without blowing other teams out the water, but the wage bill is always amongst the smallest so they’re never going to get the best players.

“So it might be the time for actually Daniel Levy, who I have been a supporter of because you look at the work he has done in terms of the stadium, but now that work is done with the stadium and training ground – someone else needs to be in charge of this football club.”

This is not the first time that the former Liverpool man has been critical of the Lilywhites hierarchy for not backing their manager in the transfer market.

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Sky Sports quotes from Carragher back in 2018 show he suggested even back then that Tottenham failed to show the kind of ambition they needed to help Mauricio Pochettino vie for the title.

The 46-year-old said at the time: “Tottenham didn’t recruit in the summer and the team we’re looking at now, I feel as if that was the team I was watching two years ago, which was brilliant, almost won the title.

“You stand still, you fall behind and I don’t think it’s sustainable, what they spend in the transfer market and getting into the Champions League year in, year out.

“That is not down to the great business sense of the club or the board, that’s to do with the brilliance of [Mauricio] Pochettino and the players that they have at this moment and what he’s actually getting out of them.”

Players now joining in the criticism of Tottenham hierarchy

It is not just pundits and Spurs fans who have called out the Spurs top brass for not investing sufficiently into the squad, but also one of their key players.

Cristian Romero did not hold back his thoughts on the club’s transfer business, insisting just a few days ago that the Lilywhites have not invested enough into the squad to equip them to challenge the best sides in the Premier League.

When asked if Tottenham had fallen behind their top six rivals in terms of investment and squad strength to compete for titles, the Spurs vice-captain said: “The truth is, I would say no comment, but… Manchester City competes every year, you see how Liverpool strengthens its squad, Chelsea strengthens their squad, doesn’t do well, strengthens again, and now they’re seeing results.

“Those are the things to imitate. You have to realise that something is going wrong, hopefully, they realise it. The last few years, it’s always the same: first, the players, then the coaching staff changes, and it’s always the same people responsible.

“Hopefully, they realise who the true responsible ones are, and we move forward because it’s a beautiful club that, with the structure it has, could easily be competing for the title every year.”

One Tottenham defender, who has not had much game time this season, is expected to be the subject of plenty of interest in the January transfer window.

Spurs man yet to start a single game

Even though Djed Spence garnered praise from Ange Postecoglou at the start of the season and was rewarded with a new four-year contract, he has had to watch on from the sidelines so far.

The 24-year-old has been restricted to just five substitute appearances across all competitions and is still waiting for his first start of the campaign.

It has now emerged that the full-back is set to be the subject of enquiries during next month’s transfer window.

Tottenham’s resolve for Djed Spence will be tested

This update comes from GiveMeSport, who revealed that parties have been put on ‘red alert’ regarding the defender, given his lack of game time at Spurs this season.

The report says that Tottenham’s resolve to hold on to Spence is expected to be tested by the right-back’s suitors next month, with a number of admirers ‘determined to discover’ if the Lilywhites will let the player go either on loan or permanently.

The outlet explains that Spurs are forcing interested parties to wait as they are delaying the final decision over his future.

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Spence’s stance on his future

GiveMeSport go on to state that Spence is trying to remain patient as he waits for an opportunity to break into Postecoglou‘s side.

However, the former Middlesbrough man is said to be wondering whether or not he fits into the plans of the Australian after warming the bench so far this season.

The publication adds that as things stand, the defender is unlikely to be handed much game time at Spurs, which is why his admirers have been given optimism about a potential January deal.

While Tottenham Hotspur may not have lifted a trophy since the 2007-08 EFL Cup, the club has frequently been at the centre of blockbuster transfers, with some of their most talented players fetching staggering sums and leaving fans wondering what could have been. Let’s take a look through Tottenham’s top ten biggest transfer sales of all-time.

Tottenham’s trophy drought and talent exodus

For a club that has long prided itself on nurturing some of the game’s finest talents, Tottenham Hotspur have endured a painful wait for silverware, with their last major honour arriving over 15 years ago.

The lack of trophies has often seen the club’s brightest stars depart in search of glory elsewhere, and many of them found exactly that after leaving north London.

From Gareth Bale’s record-breaking move to Real Madrid to Harry Kane’s recent high-profile transfer to Bayern Munich, Spurs have been no strangers to lucrative sales, with each departure stirring mixed emotions among their devoted fanbase.

The funds generated by these sales have occasionally been reinvested well but have often sparked debates over whether the club has made the most of their financial windfalls.

Despite the frustrations, Tottenham’s knack for commanding hefty fees for their departing players is a testament to the talent they have cultivated over the years.

Here, we delve into Tottenham’s top ten biggest transfer sales in the club’s history and explore the details of these headline-grabbing transfers.

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Tottenham’s top ten biggest transfer sales of all time

Signed from Burnley for just £3.5 million in 2015, Kieran Trippier quickly established himself as a dependable right-back, renowned for his pinpoint crossing and set-piece ability. His move to Atletico Madrid in 2019 was met with some surprise, yet the Englishman thrived in Spain, helping Atletico secure the La Liga title in 2020-21.

Robbie Keane’s transfer to Liverpool in 2008 brought an end to a remarkable first spell at Tottenham, where the Irish striker etched his name into club folklore. Although his time at Anfield was underwhelming, Keane made a swift return to Spurs for a fee that underscored his enduring value.

Signed for £11 million in 2013, Christian Eriksen proved to be a creative maestro during his time at Spurs, twice earning the club’s Player of the Year award. Despite his departure to Inter Milan in 2020, Eriksen’s legacy at Tottenham remains untarnished, with his contributions pivotal in their journey to the 2019 UEFA Champions League final.

Michael Carrick’s move to Manchester United in 2006 marked the end of a brief yet impactful spell at Tottenham. The deep-lying playmaker’s calmness on the ball and tactical awareness made him a prized asset, and his subsequent success at Old Trafford only highlighted what Spurs had lost. At least Tottenham managed to get a good price at the time for a player who to this day remains in the club’s top ten biggest transfer sales of all-time

After joining Tottenham from PSV Eindhoven in January 2020, Steven Bergwijn dazzled with moments of brilliance but struggled for consistency. His return to the Netherlands with Ajax proved to be a lucrative deal for Spurs, albeit a bittersweet farewell for fans who saw glimpses of his potential.

Luka Modric’s transfer to Real Madrid was the beginning of an illustrious chapter for the Croatian midfielder. Though Spurs failed to claim silverware during his tenure, Modric’s elegance and vision on the pitch made him a fan favourite, and his subsequent Ballon d’Or win validated his greatness.

The enigmatic Bulgarian forward became a household name at Spurs with his flair and clinical finishing. While his move to Manchester United broke hearts, Berbatov left behind fond memories of his spellbinding performances in a Spurs shirt.

Kyle Walker’s transfer to Manchester City in 2017 made him the world’s most expensive defender at the time, underlining his rise to prominence as one of the Premier League’s finest right-backs. Not only is he in Tottenham’s top ten biggest transfer sales of all-time, but he is also the biggest defender sale in the club’s history.

Harry Kane’s departure to Bayern Munich was a defining moment for Spurs, ending an era where the academy graduate had carried the team on his shoulders, becoming the club’s all-time top scorer. Kane scored 280 goals and laid on another 61 assists in 435 games for Spurs (TransferMarkt).

Number one on Tottenham’s list of top ten biggest transfer sales of all-time, Gareth Bale’s move to Real Madrid shattered records and ushered him into a world of galacticos. The Welshman’s electrifying performances in his final Spurs season remain unforgettable, with his name etched into club folklore.

A club of sellers or strategic rebuilders?

The Lilywhites’ top sales tell a tale of shifting strategies and ambitions over the years. While it is undeniable that Spurs have lost some generational talents, these sales also highlight the club’s emphasis on financial prudence and reinvestment. Whether these funds have been effectively utilised, however, is a question that has long divided fans and analysts.

One former Spurs defender, Ryan Sessegnon, who was signed by Mauricio Pochettino, has admitted that he barely spoke to the Argentine boss during his time in North London.

Wing-back failed to fulfil his potential at Spurs

Ryan Sessegnon was considered to be one of the best young talents in English football when he made the switch to Tottenham in 2019.

In theory, it should have been an excellent fit, given the way, pacy, young players had thrived under Pochettino.

However, instead, the left-back did not play a single game under the Argentine, who was sacked just a few months after his arrival, being replaced by a manager with a polar-opposite style in Jose Mourinho.

Ryan Sessegnon opens up on early days at Spurs

Sessegnon revealed that since he was injured in his early months at the club, he was not allowed in team meetings and was barely around the playing group when Pochettino was in charge.

The 24-year-old told Rising Ballers: “I’d just come back from the U21s Euros and I got injured in that tournament. I arrived injured. I turned up and I wasn’t training, I was in the physio room, and I didn’t have much contact with Poch or the team.

“At the time he didn’t want injured players in his meetings or stuff like that. He welcomed me to the club and all of that stuff, but I wasn’t around the players or stuff at the time.

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“By the time I got back, I went to England U21s camp in November that season, when I came back Pochettino got sacked. So I didn’t have much of a relationship with Poch, even though he brought me to the club.”

Mauricio Pochettino was never the same at Spurs after Champions League final

It is clear that something broke between Pochettino and Spurs after the 2019 Champions League final loss, with the Argentine simply not having the same energy from next season.

It is a shame as the signings that Spurs made in 2019 (Sessegnon, Giovani Lo Celso and Tanguy Ndombele) might have all thrived under the Poch, but all of them flattered to deceive under counter-attacking managers who followed.