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Tottenham Hotspur must be ready to explore the possibility of a move for Sunderland left-back Dennis Cirkin on a free transfer this summer.

The former Spurs academy graduate is facing a hugely uncertain future at the Stadium of Light, and appears set to be on the hunt for a new club this summer.

Roberto De Zerbi’s side will still be hopeful of securing their Premier League status at the end of the season, but it would be silly for them to not begin making contingency plans for the Championship.

Cirkin played a starring role for the Black Cats in their promotion from the second tier last term, and established himself as one of the division’s best full-backs with some impressive displays.

Regular gametime has deserted the 24-year-old in the Premier League this season, and the latest noises from Sunderland should be enough for him to feature in Tottenham’s summer transfer plans.

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Regis Le Bris hints at Dennis Cirkin departure as Tottenham may reignite interest

Tottenham were heavily linked with a move for Cirkin last summer, as they explored potential options to boost the number of home-grown players in their squad for Champions League registration.

Their need could be very different this time around if they are relegated, and a drop into the Championship would almost inevitably bring a huge turnover in their squad.

The Lilywhites would need to add fresh faces with proven quality at that level, who also know what it takes to secure promotion back to the Premier League, and Cirkin is somebody who ticks both of those boxes.

Regis Le Bris admitted on Thursday that he doesn’t know where the defender’s future lies ahead of his contract expiring this summer, as he added that it is “important” that he and his team “stay focused on the league.”

Cirkin may not have had much of a chance to impress in the Premier League this term, but he shone in his last Championship campaign, and there will surely be no shortage of suitors for him this summer if he does leave Sunderland.

He is a player who knows Tottenham and cares about the club, and if they do fall into the Championship for next season, then he could prove to be a shrewd acquisition for them.

Tottenham’s need for a new left-back is clear

Former Manchester United chief scout Mick Brown told Football Insider back in March that Manchester City have already held internal conversations about a possible move for Destiny Udogie this summer.

The Italian has been heavily linked with a move away from North London in several of the recent transfer windows, but this could finally be the one where he moves on, after two consecutive woeful league campaigns.

Spurs currently have Djed Spence as cover, but with his England aspirations clear to see, it would be a huge surprise if he were willing to play Championship football next term.

The left side of defence is an area that De Zerbi and Co. will need to strengthen regardless of which league the team end up in, and they could do far worse than a move for Cirkin.

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Daniel Levy is set to face further issues selling his stake in Tottenham Hotspur’s ownership group if the club are relegated this season, sources have told Football Insider.

Despite leaving his role as executive chairman in September, the 64-year-old still has an indirect investment in Tottenham due to his 29.88 per cent share in ENIC, which owns 86.91 per cent of the club.

Levy has been in talks to sell his stake, but he’s believed to be seeking a deal worth up to £1billion.

Spurs are at risk of being relegated as they currently sit third bottom in the Premier League table following their miserable campaign.

Sources say Tottenham’s valuation will drop considerably if they are relegated to the Championship, directly impacting how much Levy could receive from a potential sale.

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Who could buy Daniel Levy’s shares?

Levy was a controversial figure during his time at the Tottenham Hotspur Stadium, with many fans questioning his ambitions to take the club forward on the pitch.

Vinai Venkatesham is now in charge of the day-to-day operations following his appointment as chief executive last year, but Spurs have taken another step backwards this season.

In terms of Levy’s stake, The Telegraph reported in February he can agree a deal with whoever he wants as the Lewis family, who own the remaining 70.12 per cent in ENIC, don’t have matching rights or first refusal.

However, the former chairman’s shares hold no voting rights, place on the board or influence on matters in north London.

That poses another question around the value of his stake, particularly if Spurs are relegated to the Championship this season.

Finance expert Stefan Borson told Football Insider the Lewis family are the most likely buyers of Levy’s shares, handing them more control of matters.

How relegation could impact Tottenham’s finances

Relegation would have a devastating impact on Tottenham’s financial situation due to the difference in prize money between the top two divisions.

Spurs posted their accounts for 2024-25 last month, showing their revenue improved from £528million in 2023-24 to £565m last season.

However, Tottenham’s revenue could drop by around £200m if they lose their Premier League status this season.

Roberto De Zerbi is looking to ensure that won’t be the case, having been appointed as the club’s new manager earlier this month.

Tottenham are now preparing to take on already-relegated Wolves at Molineux on Saturday (25 April).

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Thomas Frank is seemingly edging closer to becoming the next Celtic manager amid a major shift in the betting market.

The Dane was sacked by Tottenham in February following a terrible seven-month tenure, which has left the North London club on the brink of relegation from the Premier League.

Frank remains in the thinking for several clubs looking for a manager this summer, however, with his terrific work at Brentford not yet forgotten.

The Hoops appear to be among the potential suitors for the 52-year-old, with interim manager Martin O’Neill set to leave the club upon the conclusion of the season.

The race to be named Celtic’s next manager continues to be led by Robbie Keane, but Frank is emerging as a serious contender.

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Odds shorten further as Thomas Frank eyes Celtic

Football Insider exclusively revealed earlier this month that Frank is the favourite for the Crystal Palace job, which will be vacated by Oliver Glasner in the coming weeks.

The Dane appears to have escaped his Tottenham tenure with some of his credit intact, considering the events that have taken place following his exit.

The Lilywhites won just three of Frank’s final 12 games, and the Premier League form was truly dreadful, but they at least remained competitive under the 52-year-old.

Under Igor Tudor and now Roberto De Zerbi, Tottenham have lost five of seven Premier League games, drawing two and conceding 16 goals. They were never in the drop zone under Frank, but they are now.

His time at Brentford remains the sole reason for any interest, however. The former Brondby manager took the Bees from mid-table in the Championship all the way to ninth in the Premier League.

Celtic are in need of a different type of rebuild, but Frank could be just the man to deliver it.

One major bookmaker has narrowed the former Tottenham manager’s odds from 5/1 just hours ago to 7/2, while Keane remains the favourite at 2/1.

Celtic race narrowing

Jens Berthel Askou and Roberto Martinez remain in the background of the conversation regarding the next Celtic manager, but they appear to be falling out of contention.

Motherwell have lost four of their last five games under Askou, and there appears to be a feeling growing that his appointment would be premature.

Martinez will go to the World Cup with Portugal this summer, and it remains to be seen whether decision-makers at Parkhead would be willing to wait.

Frank would provide a more instant solution, though there are also risks to be considered with both him and Keane.

One thing is for sure – Celtic must get their next appointment right, or face the wrath of the fans once more.

West Ham’s hopes of Premier League survival could take a big twist on Saturday, with multiple big games set to take place.

The Hammers are set to host Everton at the London Stadium, in a match that Nuno Espirito Santo will view as winnable.

In contrast, Tottenham Hotspur travel to bottom-placed Wolves, who were officially relegated on Monday after West Ham’s draw against Crystal Palace.

As a result, many of the Hammers’ fanbase will be praying the Old Gold side can pull off an unlikely result so that they might go five points clear.

However, in recent years, Wolves have often overcome Tottenham, and West Ham’s survival hopes could depend on this happening again.

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Wolves have battered Tottenham Hotspur in recent years

While Wolves may have declined massively since their pre-COVID success, they have continued to find success against Tottenham.

Since 2023, they have been unbeaten against Spurs, winning four of their last six meetings.

During this time, they have averaged two goals a game and have won every single match at Molineux.

In fact, the last time Wolves lost a home match to Spurs in the Premier League was back in 2021.

As a result, as long as this trend continues, West Ham will surely be a step closer to safety, no matter what happens in their game against Everton, with time running out for Tottenham.

David Sullivan and Daniel Kretinsky in behind-the-scenes battle

Former Everton chief executive Keith Wyness exclusively told Football Insider that David Sullivan and Daniel Kretinsky are battling over who controls West Ham.

This comes after Karren Brady stepped down from her role at the London Stadium.

Brady stepped down from her position as vice-chair after 16 years in the role, and was responsible for the club’s move from Upton Park to the London Stadium.

This has opened the door for Kretinsky, who could now buy a portion of the Gold family’s stake to match Sullivan’s holdings.

As a result, Kretinsky or Sullivan could now step down if they cannot agree on the key decisions at the club ahead of the summer.

It remains to be seen if relegation to the Championship will affect this, with West Ham’s future in the Premier League currently looking uncertain.

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Tottenham manager Roberto De Zerbi has failed to instil enough fight into the players in his first two games in charge, according to Keith Wyness.

The former Everton chief executive, speaking to Football Insider, still has Spurs down as favourites to be relegated from the Premier League.

De Zerbi picked up his first point in charge of the club against Brighton last time out, but it was not enough to lift Spurs out of the relegation zone.

West Ham picked up a point at Crystal Palace to stay two points above Spurs, whilst Nottingham Forest are now five points above the drop zone following their victory against Burnley.

Spurs face a crucial clash at Wolves next, who are already relegated and sit bottom of the Premier League table, in a match De Zerbi’s side will be expected to win.

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Tottenham in ‘difficult position’ as expert predicts relegation fight

Everton’s former chief Keith Wyness – who served as CEO at Goodison Park between 2004 and 2009 and now runs a football consultancy advising elite clubs – says he does “feel sorry” for Spurs, but that West Ham are currently showing more fight to stay in the Premier League.

Speaking on the new edition of Football Insider‘s Inside Track podcast, Wyness said he would bet on the Hammers staying up at Spurs’ expense right now.

He told Football Insider‘s Inside Track podcast: “We’re seeing the momentum with West Ham, although Spurs did sort of show some fight for the very first time against Brighton.

“Looking at the fixture lists, Spurs are my favourites to go down, which is a seismic event. I’ve had so many requests for my take on that because I took over Villa when they were relegated. That’s probably the last big club of that sort of scale to go down.

“Although you could argue that Spurs are bigger than Villa were. Obviously they were at the time when Villa went down. It’s a difficult position, but West Ham have that momentum. I thought they were unlucky against Palace the other night.

“I thought they played really well and really showed some attacking flair and fight and desire and that’s what I’m still not seeing from De Zerbi’s team at the moment. There’s no doubt I feel sorry for Spurs, in the sense of all the injuries they’ve had this season that have dogged them really badly.

“But nevertheless, we are where we are, and if I had to put my betting money on I’d be putting it on West Ham to stay up and Spurs to go down.”

Leicester situation provides warning for Tottenham

If relegation from the Premier League would be bad enough for Spurs, the north London club should look at the current predicament at former champions Leicester City.

Leicester have suffered back-to-back relegations, and will play in League One next season despite being backed to fight for an instant return to the Premier League at the start of the campaign.

Former Manchester City financial advisor Stefan Borson told Football Insider that Spurs would also not be guaranteed Championship promotion at the first attempt.

Spurs stars would suffer a 50% wage cut, alongside a drop in revenue, in what would prove to be a financially challenging time for the club, if they were relegated.

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Tottenham Hotspur face the “risk” of not being able to get out of the Championship at the first attempt if they are relegated this season.

That is according to former Manchester City financial adviser Stefan Borson, who exclusively told Football Insider nobody expected Leicester City to suffer back-to-back relegations to League One.

The Foxes’ relegation to the third tier was confirmed on Tuesday (21 April) after they failed to beat Hull City at the King Power Stadium.

Meanwhile, Spurs are currently set to drop down to the Championship, with Roberto De Zerbi’s side sitting third-bottom in the Premier League table, two points behind 17th-place West Ham.

Tottenham would face severe financial repercussions if they are relegated from the top-flight due to the difference in prize money in the second tier.

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How relegation would impact Tottenham financially

Tottenham posted their accounts for 2024-25 last month, showing their revenue improved from £528million in 2023-24 to £565m last season.

However, that figure would drop substantially if they are relegated to the Championship.

Speaking exclusively to Football Insider, Borson discussed how Spurs’ numbers would be impacted if they lose their Premier League status.

“You’re probably looking at almost an exact drop in the total wage bill from 50 per cent player cuts plus sales,” said Borson.

“That probably ends up matching broadly the loss of broadcast. Then it’s a question of how resilient is the commercial revenue? We don’t know.

“Matchday revenue, there are a few more games, but probably at a lower average price, so probably less take on the matchday itself.

“People will probably not always be dwelling in the ground for as long as they do currently, and even if they’re season ticket holders, maybe not turning up. You’re still getting your season ticket revenue, but you might not be getting the matchday revenue to go with it.”

Why Tottenham relegation is not ‘catastrophic’

Borson insisted the impact of relegation shouldn’t be exaggerated despite the need to return to the Premier League immediately.

“They’re going to lose some money,” said Borson.

“It’s not going to be catastrophic for one season, so people shouldn’t exaggerate what it’s going to do for one season. They’ll be okay for one season.

“Clearly, nobody expected Leicester to be where they are, so things can happen that you don’t expect. It’s not as easy to get out of that division as people think.

“That’s where the risk is for Spurs. Not in the one season in the Championship. That’s manageable. It’s broader than that.”

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Tottenham ‘confident’ Archie Gray will stay amid new transfer plan

Tottenham Hotspur are hopeful of keeping Archie Gray at the club this summer if they survive relegation from the Premier League.

Gray is on the radar of several top Premier League sides as he impresses at Spurs despite their struggles this season.

He has featured regularly under their three different managers in 2025-26 and has a bright future in the game at just 20-years-old.

Despite interest in his services, Tottenham are confident that Gray will stay in North London if they avoid relegation, as I revealed on the latest edition of Football Insider’s Transfer Insider podcast.

Spurs’ transfer plans could see a real shake-up of Roberto De Zerbi’s midfield options, with Conor Gallagher and Pape Sarr each linked with respective moves away.

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Tottenham are optimistic about keeping Archie Gray if relegation is avoided

Liverpool and Bayern Munich are two of the clubs that have been publicly linked with a move for Gray in the summer window.

He featured for half an hour off the bench as Spurs drew 2-2 with Brighton on Saturday to stay 18th ahead of a vital last five games of the campaign.

Speaking on the Transfer Insider podcast, I explained: “If Tottenham stay in the Premier League, I’m sure they’ll be confident they can keep hold of Archie Gray.

“He’s under a long-term contract until 2030 and is still only 20-years-old despite having played so many games.

“Tottenham want to build around Gray, they don’t really want to lose him but a lot will depend on what league Tottenham find themselves in next season if they can keep hold of their best players or not.”

Cristian Romero moving closer to Spurs exit after release clause reveal

Romero has been Tottenham’s best defender over the last few seasons, but may have played his final game for the club after recently being ruled out for the rest of the season with a ligament tear.

The Argentine centre-back has been linked with a move away from Tottenham for the last 12 months, but did sign a new contract last summer to tie his future down until 2029.

his own father recently revealed that Romero has a release clause in his contract which could allow him to leave for between £37.8million and £53million ahead of next season.

Sources have exclusively told Football Insider that Romero looks increasingly likely to leave Spurs in the coming months due to the clause and the prospect of relegation, with Atletico Madrid reportedly interested in his services.

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The Premier League relegation battle has taken another twist this weekend after game week 33.

Both Leeds United and Nottingham Forest picked up crucial victories, while West Ham United were forced to settle for a draw on Monday night.

Tottenham Hotspur also picked up a point, meaning they remain two points adrift in the relegation zone.

With only five games left of the season, it appears Leeds are all but safe, while Forest are arguably only one or two wins from avoiding relegation.

Now, Opta has backed West Ham to maintain their top-flight status, with Spurs seen as the most likely to join Wolves and Burnley in the Championship next season.

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Tottenham Hotspur predicted to get relegated this season

While West Ham may have felt that their point against Crystal Palace was a missed opportunity, it was another step closer to safety.

The draw ensured they moved two points clear of Spurs, whose situation grows worse by the week.

On top of this, the result also officially relegated Wolves, while Burnley are now on the brink of confirming their return to the Championship.

Now, Opta on 20 April believes that Tottenham are the most likely team to join them at 57.17 per cent.

Following this, West Ham still have a 38.03 per cent chance of going down, and are far from out of it.

The supercomputer believes Nottingham Forest and Leeds United are now all but safe, with just a 4.33 per cent and a 0.47 per cent chance of ending the season in the bottom three.

West Ham face tricky summer keeping hold of their stars

Former Manchester United scout Mick Brown has exclusively told Football Insider that Jarrod Bowen is attracting interest from Liverpool and Chelsea ahead of the summer transfer window.

The Hammers captain has been one of the best players at the club consistently for years, and his form has continued this season despite their battle for survival.

The 29-year-old loves the club and currently has no plans to leave, but would be reluctant to play in the Championship.

As a result, survival could be paramount if West Ham want to keep hold of Bowen for the 2026-27 campaign, with the next five games set to decide their fate.

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Tottenham Hotspur midfielder Pape Matar Sarr looks set to leave the club this summer with a big move on the horizon if he impresses for Senegal at the World Cup.

Sarr is attracting attention from numerous top clubs ahead of the summer window despite an inconsistent season at Spurs.

The 23-year-old is set to star for his country at this summer’s tournament, with Tottenham resigned to losing his services if they are relegated from the Premier League.

As I revealed on the latest edition of Football Insider’s Transfer Insider podcast, they could be forced to cash in on Sarr if they are preparing for life in the Championship next season.

Spurs’ transfer plans will hinge on what happens between now and the end of the campaign, with Sarr likely to garner even more interest if he shines at the World Cup.

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Pape Matar Sarr exit is very likely if Spurs are relegated

Sources have exclusively revealed to Football Insider that Bayern Munich and Real Madrid are interested in Sarr, with recent reports claiming that PSG are also keen on a move.

He is set to command a sizeable fee if he does depart, with the World Cup likely to play a big part in where he could end up if Spurs are relegated this season.

Speaking on the Transfer Insider podcast, I explained: “He’s obviously a big player for Senegal, and if he goes away to the World Cup and does well for them at the finals, it’s only going to enhance his reputation and maybe bring even further interest in him.

“If Tottenham were to get relegated from the Premier League, it’s inevitable that they’re going to lose some of their top players.

“I’m sure clubs are waiting and ready to pounce if that does happen, and Sarr will be one of those players that clubs will be looking at.

“Although he’s under contract until 2030, Tottenham might reluctantly have to cash in on him if they do (get relegated).”

Conor Gallagher could leave Spurs as Everton eye loan move

Fellow midfielder Gallagher joined Tottenham from Atletico Madrid in January, but has struggled to make an impact as they battle the drop this season.

The 26-year-old has started nine of his 11 league appearances for the club so far, and despite his struggles, he was lauded for an improved showing against Brighton on Saturday.

Sources have revealed to Football Insider that Everton are interested in signing Gallagher this summer to bolster their midfield ranks, with a loan-to-buy deal possibly on the cards.

He is another star who could leave North London regardless of whether they are relegated, but he looks set to be a key man under Roberto De Zerbi as Spurs fight to survive.

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Tottenham Hotspur could save £145million on wages if they are relegated from the Premier League this season.

That is according to former Manchester City financial adviser Stefan Borson, who exclusively told Football Insider Spurs’ top-five earners are likely to leave if they drop down to the Championship.

It has been revealed the majority of Tottenham’s squad have relegation clauses that would see their wages drop by around 50 per cent in the second tier.

Roberto De Zerbi’s side currently sit third-bottom in the top-flight table, one point behind 17th-place West Ham, who have a game in hand.

Tottenham’s revenue would drop significantly if they lose their Premier League status, undoing years of work put in to improving the club’s financial situation.

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Why Tottenham will instantly lose £145m after relegation

Tottenham posted their accounts for 2024-25 last month, showing their revenue improved from £528m in 2023-24 to £565m last season.

Meanwhile, the north London giants’ wage bill increased from £222m to £256m across the same period.

Speaking exclusively to Football Insider, Borson discussed how Tottenham’s wage reduction clauses will mitigate the drop in revenue they could face in the Championship.

“It’s not going to deal with the whole lot because it’s a very big organisation,” said Borson.

“Although the players might be on 50 per cent wage cuts, I very much doubt the general staff will be on any wage cuts. You’re talking about saving let’s say £90-100m on the first-team squad for the season.

“But you’re going to lose straight away versus this season £145m if you’re relegated because this season they’ve got Champions League and they’ve also got Premier League money.

“That’s going to reduce substantially, so those two things aren’t going to match. But they will have more matchdays. Can they sell the ground out? If there’s momentum and they’re doing okay, maybe they can.”

Which players could leave Tottenham after relegation?

Borson insisted the likes of Cristian Romero and Micky van de Ven would leave if Tottenham are relegated this season.

“There are players that are going to leave,” said Borson.

“Let’s say the top-five earners, who are probably Romero, Van de Ven, Maddison, Kulusevski maybe, these sorts of players, they’re going to go.

“I would think at least three of the top-five earners are going to go. By the time you do all of the work on what it looks like, you’re going to cut the wage bill a lot.

“The wage bill is going to go from an organisational wage bill this season of let’s say £250m down to £100-105m maybe, which actually as it happens is £145m that we just talked about.

“You’re probably looking at almost an exact drop in the total wage bill from 50 per cent player cuts plus sales. That probably ends up matching broadly the loss of broadcast.”

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