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There are two Champions League fixtures that Tottenham Hotspur fans will keep a close eye on this week as they await to learn their round of 16 opponents.

Spurs finished fourth in the league phase of the Champions League and sealed direct qualification to the round of 16 stage.

As a result of finishing in the top four, Tottenham will be playing the second leg of their round of 16 and quarterfinal ties at home.

Spurs know they will play one of Juventus, Atletico Madrid, Galatasaray, or Club Brugge in the next round, which is why two fixtures will be of particular interest to the Lilywhites over the coming days.

Tottenham fans hoping for Champions League upsets this week for easier R16 draw

Galatasaray hosts Juventus at the Rams Park tomorrow for the first leg of the round of 16 playoff on Tuesday.

The Turkish giants, who are a formidable side at home, will be hoping to take an advantage into the second leg at the Allianz Stadium next week.

On Wednesday evening, Club Brugge will host Atletico Madrid in the first leg of their playoff tie at the Jan Breydel Stadium in Brussels.

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With the winner of one of those two ties set to face Spurs in the next round, the Premier League side will hope that the two minnows can pull off an upset at home in the first leg and give themselves a shot at knocking out the Serie A and La Liga giants.

When will Spurs learn their round of 16 opponents?

The draw for the round of 16 stage will take place on Friday, 27 February, after all of the playoff ties are concluded next week.

The two Round of 16 ties will be played on March 10-11 and 17-18, which means that the Lilywhites still have almost a month to prepare.

AC Milan have named their price as Tottenham Hotspur continue to track Christian Pulisic ahead of the summer transfer window.

Plans for the summer window are already beginning to take shape for Tottenham Hotspur, who need to bolster their squad.

We reported earlier in the week that Christian Pulisic is one such player who is currently on the radar of Spurs as they aim to strengthen their attack.

Such links are rather interesting given that Mauricio Pochettino has also been linked with a return to Tottenham. Poch is currently Pulisic’s national manager for the men’s USA team, and it remains to be seen whether that is a pure coincidence.

Tottenham target Christian Pulisic as AC Milan set asking price

CaughtOffSide has now revealed how much AC Milan are willing to accept in the summer window if they are to sell Pulisic.

According to their report, the Serie A club is open to listening to offers in the £60-70 million range for the 27-year-old American winger.

Milan themselves are preparing for a major squad overhaul at the end of the season, and it is claimed that the £60-70 million figure is one that could provide Milan with both financial flexibility and balance as they reshape the team.

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Spurs face Premier League competition for Pulisic

Spurs, however, are not alone in their pursuit of the former Chelsea man, with Arsenal and Manchester United also in the mix.

The wide forward, often deployed as a second striker this season, has impressed, managing ten goals in Serie A this season.

However, the player’s injury concern could be a worrying sign for Spurs, who themselves struggle to keep players fit during the course of a season.

A former Tottenham Hotspur official has revealed that Spurs are fans of an English midfielder, but a deal may not be easy to complete in the summer.

The Spurs midfield still looks in need of reinforcements, and that is an area that the Lilywhites may prioritise strengthening in the summer.

Reports indicate that Adam Wharton has emerged as Tottenham’s dream midfield target, but the Lilywhites are not the favourites to land the Crystal Palace star.

It has now emerged that the North Londoners are turning their attention to a 26-year-old midfielder who is impressing in the Premier League this season after returning from his injury layoff.

Tottenham eyeing move for Everton’s Kiernan Dewsbury-Hall

Spurs have been long-time admirers of Kiernan Dewsbury-Hall, who was first linked with a move to N17 back in 2024 when he was at Leicester City.

After struggling to make an impact at Stamford Bridge last season, the midfielder joined Everton last summer and has now established himself as a key player in David Moyes’ midfield.

It has now been revealed by former Tottenham scout Mick Brown that the Lilywhites could reignite their interest in the midfielder.

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Brown told Football Insider about Dewsbury-Hall: “Kiernan Dewsbury-Hall has done an outstanding job at Everton. He was a player I liked when I first saw him play, and I’m not surprised he’s been a success under David Moyes because he brings something new to that team.

“They’ve got a lot of solid and reliable players, but he’s got this ability to run and drive with the ball which not many others in that team have got.

It takes the pressure off the rest of the team and gives them something else going forward.

“So that’s why the interest is there, Tottenham have been looking at him, for example. They want that type of player and feel he would fit the profile if he was available, the problem is I don’t think he’s going to be available.”

Everton expected to reject any Spurs offer for Dewsbury-Hall

The former Leicester man has scored five times and provided four assists in 19 Premier League outings this term for the Toffees.

Brown believes that Everton will not be receptive to any offers for the 26-year-old when the transfer window reopens in the summer.

The former Spurs scout added: “Dewsbury-Hall is such an important player for Everton, especially if they’re going to lose Jack Grealish, and it would take a lot for them to let him go.

“I don’t think it’s something they’re going to consider because they’re not in a position where they might have to sell, it’s not like they’re in relegation trouble. They’ll be doing everything in their power to keep him at the club.”

We find out whether Tottenham’s set-piece coach, Andreas Georgson, who was appointed last summer, will stay with the club or follow Thomas Frank out the door.

Spurs’ decision to part ways with Thomas Frank did not come as a surprise following the Lilywhites’ 2-1 loss to Newcastle last week.

That was the eighth consecutive Premier League fixture in which Tottenham had failed to register a win, and the hierarchy decided to take advantage of the week-and-a-half break to make a big change at the top.

Igor Tudor has been confirmed as Spurs’ interim head coach until the summer, and the Croat has brought some members of the staff with him.

Will set-piece coach Andreas Georgson leave Tottenham?

It has been reported that Justin Cochrane, John Heitinga and Chris Haslam will leave Hotspur Way, along with analyst Joe Newton.

That is according to Alasdair Gold, who also shared that Ivan Javorcic will join as Tottenham’s assistant coach, Riccardo Raganacci as the physical coach and Tomislav Rogic as the goalkeeping coach until the end of the season.

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However, The Athletic has revealed that set-piece coach Andreas Georgson will remain at Hotspur Way, as well as the individual development coach Cameron Campbell, even though the pair were appointed after Frank’s arrival.

Even more interestingly, the outlet states that Goalkeeping coach Fabian Otte is expected to remain despite the arrival of Rogic.

Why Spurs are right to keep hold of Georgson

The biggest improvement Tottenham made under Frank was arguably their set-piece play, both in terms of attacking and defending.

According to The Times journalist Hamzah Khalique-Loonat, Tottenham have scored the joint-second most goals from set-pieces in the Premier League this season, with 13.

Meanwhile, they have only conceded seven goals from set-pieces, which is the joint-sixth fewest across the division.

There has been an update on Guglielmo Vicario’s transfer stance ahead of the summer transfer window as the interest in the Tottenham number one continues to intensify.

Many have questioned if Vicario is good enough for Tottenham, with the Italian continuing to make some unforced errors from time to time, although his shot-stopping has remained of very high quality.

With reports indicating that Spurs are eyeing an ambitious squad rebuild in the summer window, the goalkeeper may potentially be on his way out in the summer.

It has been widely reported that Inter Milan will try to sign the Tottenham star at the end of the season, and just a couple of days ago, it emerged that Juventus have joined Inter in the race for the Spurs man.

Guglielmo Vicario wants to leave Tottenham in the summer

A fresh update from Gazzetta dello Sport has backed up the claim about both the Nerazzurri and the Bianconeri battling it out for the goalkeeper.

The report says that Vicario is now ‘eyeing a return to Serie A’ after three years in North London.

The ‘significant transfer duel’ between Inter and Juve could intensify over the coming days, with the San Siro club able to offer the 29-year-old ‘more favourable terms’.

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However, the report adds that ‘the player’s desire could change things’ and put Juve back in the running, which potentially hints that the Tottenham Hotspur number one may be leaning towards a move to the Allianz Stadium.

How much will Spurs demand for Vicario?

Gazzetta say that Inter have been ‘mulling over’ a move for the Italy international goalkeeper for some time, but they know that it would require ‘ideal conditions’ to complete the transfer.

With Vicario’s deal at Spurs running until 2028, the Premier League side are said to be demanding over €30m (£26m) for the former Empoli man.

Tottenham Hotspur are fans of a Serie A defensive midfielder, who may be bound for a move to England in the summer.

Despite Tottenham bringing Conor Gallagher through the door in the summer, the Spurs midfield still looks in need of reinforcements, seemingly lacking when it comes to ball progression.

Reports indicate that the Lilywhites have identified Crystal Palace’s Adam Wharton as their dream summer signing, but a deal for the 21-year-old may be hard to complete, given that Tottenham look unlikely to qualify for next season’s Champions League.

Spurs may thus need to turn their attention to more realistic targets, and they have now allegedly identified a Parma midfielder as an option.

Tottenham eyeing summer move for Parma’s Mandela Keita

According to a report in Parma Today, Mandela Keita has emerged as a target for the Lilywhites ahead of the summer window.

The Belgian international, who arrived from Royal Antwerp in August 2024, has become a key player for manager Carlos Cuesta and is delivering consistent displays in the base of his midfield this term.

This has not gone unnoticed in England, with Tottenham monitoring Keita for a while. In fact, it is revealed that officials from the North London club have scouted the 23-year-old regularly this season.

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Two other clubs could challenge Spurs for Kieta

Parma today say that Tottenham have been joined by Aston Villa in the race for the defensive midfielder, while Napoli have also been fans of the player.

The title of the report states that the ‘Premier League awaits him’, which suggests that Spurs and the Villans may be ahead in the race for Kieta.

With the former Antwerp man’s current deal running until 2029, it would take at least €25m (£21.7m) to price him away from Parma in the summer.

There has been a very interesting update from Italy over the future of a centre-back who is rumoured to be on Tottenham’s radar.

According to some reports, Spurs are fearful of losing both Micky van de Ven and Cristian Romero in the summer on the back of a poor campaign domestically.

While Tottenham Hotspur are expected to fight to keep hold of both players, one would expect the club to make contingency plans if one of them potentially decides force their way out.

An Inter Milan centre-back has been on Tottenham’s radar since last summer, and there has now been a fresh update on his future.

Sizable offer expected to arrive for Tottenham target Yann Bisseck

The player in question is Yann Bisseck, who is thought to be intrigued by the idea of joining Spurs, according to an earlier report from Gazzetta dello Sport.

A new report in FC Inter News now suggests that the German centre-back may indeed be bound for England at the end of the season.

It is revealed that an unnamed Premier League club is ready to make an offer of €40m (£34.7m) for Bisseck in the summer.

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The outlet also reveals that Crystal Palace’s efforts to sign the 25-year-old were rebuffed during last summer’s transfer window.

How much is Bisseck likely to cost?

FC Inter News say that while the expected £35m offer is a ‘significant figure’ for the Nerazzuri, that may not be enough to convince them to sell.

It is explained that if Bisseck makes it into the German squad for the World Cup and performs well in the tournament, his value could shoot up even further.

Leeds United have joined the race for a £30m-rated Championship midfielder, who Tottenham have long been interested in.

There is no denying the fact that Tottenham Hotspur currently have very similar profiles of players in their midfield.

Joao Palhinha and Yves Bissouma are almost of an identical mould – players willing to sweep things up in the middle of the park and protect the defensive line.

There is also an argument to be made that Rodrigo Bentancur, Pape Matar Sarr, and Conor Gallagher are of a similar profile, which sparks the need for variety.

Tottenham eye Hayden Hackney as Leeds join transfer race

There have been talks of Tottenham showing interest in Middlesbrough midfielder Hayden Hackney, who is of a different profile to what Spurs currently have in midfield.

That interest dates back to last summer, but no agreement has been reached, with the 23-year-old staying put at Boro.

A fresh report from Alan Nixon now states that Tottenham Hotspur have one more Premier League club to worry about, with Leeds showing interest in signing Hackney in the summer window.

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Daniel Farke’s men will obviously have to get in line, as Spurs, Manchester United and Everton could also make a move for him this summer.

Previous reports have suggested that Boro want £30m to sell Hayden Hackney this summer.

The Boro midfielder is currently enjoying a stellar campaign from defensive midfield, having scored four goals and managed six assists in 31 Championship appearances, which is a lot more than any of Spurs’ holding midfielders in the Premier League.

However, with Middlesbrough on course for promotion, topping the Championship table, they could well secure a far more significant fee for the midfielder should they return to the Premier League.

Hackney, on the other hand, has just one year left on his current contract, leaving the Championship side with next summer as the last time they can demand a significant fee if he does not sign an extension.

Igor Tudor has decided on his three Tottenham coaches, but that means four others follow Thomas Frank out of the exit door.

Spurs relieved Frank of his duties just eight months after his arrival in the summer, with the Dane leaving Tottenham just five points off the relegation zone.

Igor Tudor has been confirmed as Spurs’ interim head coach until the summer, and the club will hope that the former Juventus manager’s arrival will uplift the squad.

Tudor has experience of galvanising struggling sides mid-season, and the 47-year-old is set to bring his own staff with him.

Three coaches set to join Igor Tudor’s staff at Tottenham

Alasdair Gold has now revealed that the former Juventus boss will be accompanied by three members of the staff he has worked with at the Allianz Stadium.

Subject to their work permits being cleared, Ivan Javorcic will join as Tottenham’s assistant coach, Riccardo Raganacci as the physical coach and Tomislav Rogic as the goalkeeping coach until the end of the season.

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Gold adds that Justin Cochrane, John Heitinga and Chris Haslam, who were part of Frank’s staff, will leave Hotspur Way, as will analyst Joe Newton.

The journalist wrote on X: “Igor Tudor’s coaching staff will include, subject to work permits, Ivan Javorcic as assistant coach, Riccardo Ragnacci as physical coach and Tomislav Rogic as goalkeeping coach. Leaving Spurs are Justin Cochrane, John Heitinga and Chris Haslam, along with analyst Joe Newton.”

Tudor has been written off already ahead of Spurs adventure

Tottenham legend Teddy Sheringham has said that he is flabbergasted by the club’s decision to appoint Tudor temporarily.

Sheringham pointed to the former Juve boss’s lack of Premier League experience and suggested that he may be in for a rude awakening at N17.

Tottenham Hotspur have secured the signing of an England U16 captain as they continue to strengthen their academy at the expense of Chelsea.

The winter transfer window has since slammed shut, and it was labelled one of the worst transfer windows by Spurs fans, given the club’s lack of activity.

The signing of Conor Gallagher and Souza was the piece of business done by Tottenham, as they failed to strengthen an injury-hit squad with further additions.

However, a few youngsters were also signed for the academy, with Tottenham agreeing a deal for West Ham United academy forward Elisha Sowunmi, an 18-year-old capable of playing anywhere across the front line.

Tottenham complete signing of England U16 captain George Jobling

It has now been revealed that Spurs have moved once again to secure the signing of a highly rated youngster for their academy.

It is understood that Tottenham have completed the signing of highly regarded England U16 captain and right-back George Jobling, formerly of Chelsea.

The 15-year-old previously featured for the Chelsea U16 setup and has also made six appearances for the England U16 side.

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These signings continue to arrive after Vinai Ventaksheman stated that focus is also expected to shift towards growing the Tottenham youth setup.

Spurs youth focus grows amid academy pathway concerns

Of course, there is a growing need for Spurs to turn their attention to securing promising talents, given that no academy star is currently a mainstay in the Tottenham first-team squad.

Tim Sherwood has warned that if Tottenham do not rely on youth, they could well miss out on another Harry Kane.