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Tottenham Hotspur full-back Andy Robertson has given Roberto De Zerbi a real selection headache after making history for Scotland on Saturday night, as he put on a barnstorming display against North Macedonia.

Robertson became only the second-ever Scotland player to reach 100 caps, following in the footsteps of Celtic and Liverpool legend Kenny Dalglish.

The 32-year-old has been one of Tottenham’s better players in a disastrous start to the new season for De Zerbi‘s men, who currently sit bottom of the Premier League table after five games.

Having signed on a free transfer from Liverpool over the summer, he has silenced any doubters regarding his ability to still be a regular starting left-back in the English top flight during the latter stages of his career.

And his display in Skopje will have thrilled De Zerbi, with the Scottish media waxing lyrical about the veteran left-back after goals from Kieron Bowie and John McGinn sealed an impressive win.

The Scotsman wrote: “A landmark game for the captain as he won his 100th cap. He was mightily impressive until the 83rd minute when a short pass put McKenna in trouble, otherwise his mark would be higher.

“Rampaged up the left flank and looked in the mood to score, with three efforts raining down on Dimitrievski. A night to remember for a Scotland legend. Eight.”

The National stated: “A performance befitting of becoming Scotland’s second-ever centurion.

“Showed his intent with four strikes in the first half as he blitzed forward and caused North Macedonia problem after problem. Rarely challenged defensively, meaning he had the freedom to charge forward and do his best work in the opposition half.

“A professional display, especially after Scotland reduced to ten, in the words of James McFadden, ‘A man possessed’. Eight.”

Finally, the Scottish Sun wrote: “Joined King Kenny as Scotland centurion. Close to bagging fifth Scotland goal on big night after just four minutes but fierce strike was tipped over. Went close again twice in fittingly polished display…Eight.”

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De Zerbi facing Tottenham selection dilemma

The Italian now faces a massive call when domestic action resumes after the three-week international break, with Tottenham heading to Manchester United on October 10.

While Robertson has started the majority of games under De Zerbi so far this season, Destiny Udogie will be fresh and raring to go, having been training at Hotspur Way after being snubbed by Italy this time around.

Udogie is the more defensively sound, and it would come as no surprise if he was favoured over the more attack-minded Robertson for the game at Old Trafford.

Either way, De Zerbi faces a tough choice in a game where Spurs will be desperately seeking their first three points of the campaign against a United side also struggling under Michael Carrick.

Indeed, there is the slim possibility that the loser of this game could end up being savked, given the growing pressure on both managers.

Tottenham have decided whether or not to sell Micky van de Ven to Liverpool amid reports the Reds are lining up the Dutchman as Virgil van Dijk’s heir.

Van Dijk remains one of the best centre-halves in the world, though he’s out of contract next summer and turns 36 around that time.

It’s as yet unclear whether Liverpool will offer a new deal, and if they do, whether it contains terms Van Dijk would deem acceptable. He’s currently the highest earner at the club, and by some margin too.

In any case, the Reds already have one eye on the future, which is only natural given Van Dijk’s age.

A recent report from CaughtOffside claimed Liverpool have lined up Tottenham ace, Micky van de Ven, as Van Dijk’s heir.

They declared: ‘Sources close to the agents industry have informed CaughtOffside that Liverpool’s interest appears particularly significant.

‘The Reds are already planning for life after Virgil van Dijk, whose minutes are being managed more carefully this season, and Van de Ven fits the profile of a potential long-term successor.’

On the subject of cost, it was stated sources within the industry believe Van de Ven – who signed a contract extension with Spurs in August – could move for a figure in the £80m-£90m range.

At that price, Van de Ven would surpass Harry Maguire as the world’s most expensive defender.

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Tottenham decision on selling Micky van de Ven to Liverpool

But according to the latest from Football Insider’s Pete O’Rourke, Spurs fans need not fear the club selling their best defender.

O’Rourke stated: ‘Tottenham have no plans to sell Micky van de Ven as Liverpool prepare to move for his services next year.’

He added: “Tottenham are quite relaxed about this. They tied down Van de Ven to a new contract in August until 2031.

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“So look, Tottenham hold all the aces here, he’s been made club captain as well, so I can’t imagine they’ll be too keen to lose such a key player.

“Tottenham won’t be entertaining a sale anytime soon. Top players will always attract interest and have suitors, but he’s under a long-term contract at Tottenham and they’re planning for life with Mickey van de Ven.”

Tottenham Hotspur insider Alasdair Gold has delivered some interesting observations from training this week when it comes to forgotten man Dejan Kulusevski and summer signing Tosin Adarabioyo.

There is growing optimism at Spurs about Kulusevski’s return, as the Swedish attacker enters ramps up his rehabilitation after more than 500 days out of action.

The extended international break has given the 26-year-old some crucial extra time to work towards full fitness, with some reports suggesting that Kulusevski could finally be ready to feature over the coming weeks.

According to reports, Kulusevski’s progress has lifted the morale of his teammates at Hotspur Way, as Tottenham attempt to haul themselves off the bottom of the table after a disastrous start to the new season.

While the Sweden international did feature as a No.10 at times under Ange Postecoglou’s management, he has nominally been a right winger during his time at the club.

But, after watching the latest training video released by Spurs, Gold pointed out that Kulusevski was training to play centrally rather than out wide in what could be a more defined role for him going forward.

Gold wrote in Football.London: “The 26-year-old looked bright in the training footage from this week and set up teammate Mohammed Kudus for a couple of goals with some incisive passing.

“Despite the Ghanaian having been at Spurs for more than a year now and suffering from his own long-term injury, the two attackers have never played in a game together.

“With Kudus operating down the right and Kulusevski feeding him the ball into his runs in the small-sided mini-games, could Kulusevski be the number 10 De Zerbi turns to when he’s fully fit, with Maddison and eventually Xavi, rather than his more regular role as a right winger before his injury?”

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Tosin standing out from the crowd

Meanwhile, Gold was also struck by what he saw and heard from one of Tottenham’s last summer signings in Tosin.

He stated that the former Chelsea man’s voice could be heard throughout the four-minute video, suggesting that Tosin is the sort of vocal presence that Spurs have lacked in their backline, alongside his physical presence – especially after Jan Paul van Hecke was bullied by Aston Villa’s Nicolas Jackson last time out.

Gold added: “There was one noticeable player voice constantly heard during the training sessions, and that was summer signing Tosin Adarabioyo.

“In the training footage shown this week, Adarabioyo was constantly talking to those around him and barking instructions at his teammates, young and old.

“Spurs need some strong voices and personalities in the squad, and they could need the former Chelsea and Fulham defender in the weeks ahead as Jan Paul van Hecke has suffered a toe injury.”

Brazil legend Roberto Carlos has lavished praise on a ‘top-level’ Tottenham Hotspur youngster who was packed off on loan during the summer transfer window, after becoming surplus to requirements by Roberto De Zerbi.

The Italian made a conscious effort to add more Premier League experience to his defensive line over the summer, landing the likes of Andy Robertson, Marcos Senesi, Jan Paul van Hecke and Martin Dubravka.

The addition of Robertson in particular enabled Tottenham to cash in on wantaway England star Djed Spence, with the 32-year-old forming a tandem with Destiny Udogie in the left-back position.

That left Brazilian talent Souza out in the cold as a result, with the 20-year-old having arrived from Brazilian side Santos in January in a £13million deal.

At the time of signing, then Spurs boss Thomas Frank stated that the club believed they had “bought one of the brightest left-back talents in the world who can give us something now but also for the future”.

However, Souza only managed to chalk up four first-team appearances, having swapped one relegation battle in Brazil for another in England.

Illness then interrupted the defender’s pre-season and he was ultimately left out of De Zerbi’s tour squad for the trip to New Zealand and Australia, in order to build his fitness back up.

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Souza surplus to requirements at Tottenham

And with Robertson and Udogie ahead of him in the pecking order, De Zerbi gave the green light for the talented youngster to head out on loan to Portuguese outfit Porto.

While Souza has yet to make his debut for Porto, injuries look set to hand him that chance soon, with boss Francesco Farioli reportedly working with the young defender on the training pitches to adapt him to his system. Indeed, Porto are set to play Deportivo La Coruna in a friendly on Friday and the Spurs man is expected to feature.

And, having been asked about Souza at the Portugal Football Summit this week, former Real Madrid star Roberto Carlos made it abundantly clear that he believes all the hype in his homeland about the Tottenham starlet will eventually be realised.

“I don’t like to make comparisons. He came to Porto because he has quality. He’s a player who played extremely well at Santos, it was a great signing,” said the 53-year-old as reported by O Jogo.

“I’m absolutely certain that he will deliver what is expected of him on the field, he’s a top-level player.”

Tottenham will be hoping that Souza is handed significant game time for the rest of the season, in order to develop, return to the club and then challenge for a starting role in 2026/27.

Kim Min-jae’s future at Bayern Munich is back under discussion, with sources indicating the Bundesliga champions are open to selling the South Korean international if the right offer arrives, amid interest from Tottenham and Aston Villa.

The 29-year-old centre-back remains under contract until 2028, yet he has slipped to third choice behind Dayot Upamecano and Jonathan Tah under Vincent Kompany. TEAMtalk understands that his reduced role has encouraged clubs elsewhere to keep watching.

Tottenham, Aston Villa and AC Milan all made contact over him in the summer without lodging a formal bid, and all three remain interested. Sources have also stated that Juventus are among the sides monitoring his situation.

Nothing is advanced. The player himself has been described as content to stay and comfortable with his current squad role, even if starts are limited.

Over the summer, he is understood to have turned down interest from Aston Villa and a tentative enquiry from Nottingham Forest.

Even so, the prospect of a sale has not gone away. We understand that Bayern are open to letting him leave this summer or in January if they sign a new centre back, and the clubs already in contact are expected to revisit the situation once the direction is clearer.

A January move is regarded as more unlikely; the more realistic window is next summer, when Munich could still command a fee rather than risk his value falling further.

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Tottenham, Aston Villa keen on Kim Min-jae

We understand that a bid of £30million will be enough to secure Min-jae’s signature next summer.

For Tottenham and Aston Villa, he offers Premier League-ready experience and a proven profile earned during Napoli’s 2024/25 Serie A title win, in which he played a crucial role.

Milan and Juventus know Min-jae well from Italy, too, and continue to admire him.

Whether any of them turn monitoring into a bid will depend on Bayern’s stance, contract talks and any potential incomings.

Crucially, it will also depend on whether the defender, for all his willingness to stay, is ultimately told he needs to find a new club and has no place in Vincent Kompany’s plans moving forward.

Min-jae has made three of a possible four Bundesliga appearances this season, but has missed out on a place in the starting XI twice, with Jonathan Tah picked ahead of him.

In Tottenham’s case, their chances of signing a top-class defender like Min-jae will of course depend on them staying in the Premier League.

Spurs currently sit bottom of the Premier League table after picking up just two points from their five matches so far, with Roberto De Zerbi coming under significant pressure.

Kaoru Mitoma is emerging as what sources describe as a solid market opportunity with his deal at Brighton nearing its conclusion, and with TEAMtalk understanding that a reunion with former boss Roberto De Zerbi at Tottenham Hotspur is one possible outcome.

Mitoma’s long-term future at the AMEX has grown increasingly uncertain, with the Japan international entering the final season of his contract and talks over a fresh deal showing little sign of progress.

The 29-year-old winger agreed a four-year extension in October 2023 that runs until 30 June 2027, an agreement that places him among the club’s higher earners on roughly £80,000 a week.

Manager Fabian Hürzeler confirmed in March that discussions had taken place and expressed hope that Mitoma would commit to an extension on the south coast.

However, talks with the 67-goal winger have since stalled and, as we revealed earlier last month, sources close to the situation indicate the player is reluctant to sign further terms, partly because of interest from elsewhere, and with a painful exit now beckoning.

Several UEFA Champions League clubs are understood to have made contact during his summer rehabilitation, exploring the possibility of a free transfer in 2027.

With only 91 days remaining once the January window opens, Brighton face the familiar choice of selling at a reduced fee or risking losing a key asset for nothing, and with Tottenham and Liverpool both monitoring the situation carefully, though they are far from the only clubs keen…

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Mitoma has interest in England and overseas

Liverpool have retained a long-standing interest in Mitoma.

Their recruitment staff rated Mitoma highly before his move to Brighton from Kawasaki Frontale, and more sources have linked Anfield with monitoring his situation as the contract winds down.

Tottenham have also been mentioned, both earlier this year and again in September, with the connection to Roberto De Zerbi, who previously managed Mitoma on the south coast, adding an extra layer and relationship.

While De Zerbi has invested heavily at Spurs, the club are yet to see an uptick in form and the addition of Mitoma for a cut-price fee in the winter window could prove extremely handy over the last half of the season.

Spurs, meanwhile, have also been linked with another top Asian forward, with Son Heung-min recommending his South Korean teammate to the club as a possible striker target.

With regard to Mitoma, Arsenal have been interested previously, though no formal approach has ever been made. Chelsea and Manchester United have featured in older links, albeit minus recent concrete movement.

On the continent, Bayern Munich remain the name that surfaces most often. The German champions are said by sources to have watched him extensively and held talks with his representatives in previous windows.

Atlético Madrid were also credited with an interest before moving for another target but are not closed off from moving for him on a free. There is also interest in Turkey, though sources have stated that they would need to work to convince Mitoma to move to the Super Lig.

Mitoma’s availability is further complicated by his fitness, however.

A hamstring injury suffered in May ended his 25-26 campaign and ruled him out of the World Cup; he is still working his way back under a cautious timetable set by Hürzeler.

Until he returns and shows his best form, any January interest is likely to be less than in previous seasons, heightening the prospects of a free transfer move away next summer instead.

AC Milan have offered Fikayo Tomori and Ruben Loftus-Cheek to several Premier League clubs ahead of the January transfer window, with Tottenham Hotspur and Coventry City in the mix to sign the duo, TEAMtalk understands.

The England internationals are both entering the final six months of their contracts at San Siro, with neither player’s camp having yet held talks with Milan over a new deal.

That has opened the door to potential January exits. We understand Milan are willing to do business on both players as they look to create space in their squad and give themselves greater room for manoeuvre in the January market.

Tomori, 28, has yet to feature for Milan this season, while Loftus-Cheek, 30, has slipped some way down the pecking order.

With both players out of contract at the end of the season, Milan are now prepared to explore their options rather than risk losing them for nothing next summer.

Whether a January move would be permanent or initially take the form of a loan remains to be seen.

However, we understand that intermediaries have spoken to a host of clubs about the availability of the former Chelsea pair, with Tottenham, Newcastle, Everton, Crystal Palace, Nottingham Forest, Sunderland and Fulham all contacted.

Spurs have endured a disastrous start to the season and currently sit bottom of the Premier League table after five games – their worst start to a campaign for 18 years.

They already have one eye on the January transfer window, in case Roberto De Zerbi is forced to bring in further reinforcements to avoid a potential relegation battle.

The opportunity to bring in two experienced players in Tomori and Loftus-Cheek on cut-price deals could prove tempting. However, newly promoted Coventry are ones to watch in the race, too.

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Frank Lampard keen to bring Tomori, Loftus-Cheek to Coventry

Coventry are understood to hold significant interest in Tomori and Loftus-Cheek.

We can reveal that Frank Lampard would be keen on the opportunity to reunite with the duo, having worked with both players during their Chelsea careers.

Milan’s willingness to listen to offers comes as they look to reshape their squad ahead of the second half of the season.

Both Tomori and Loftus-Cheek have considerable Premier League experience and could represent attractive options for clubs looking to strengthen in January.

Tomori has previously established himself as a key defender at both Chelsea and Milan, while Loftus-Cheek offers versatility in midfield and has also operated in more advanced roles.

For Milan, moving either player on would help create additional room within the squad and potentially allow them to pursue further business in January.

The Rossoneri are therefore prepared to consider proposals, with the possibility of loans also on the table as the January window approaches.

Tottenham legend Son Heung-min has reportedly recommended South Korea teammate Oh Hyeon-gyu to the club, with Spurs identifying him as a priority target, it has been claimed.

Spurs are having a terrible time in front of goal this season. After five Premier League games, they’ve scored just twice, and neither goal has come from a forward.

There’s a suggestion that they’re going to look at the final third again in January to rectify the problem, despite spending big on Savio and loaning in Omar Marmoush, whose deal will become permanent in the summer.

Per Turkish Football, Tottenham have identified Besiktas striker Oh as a primary central target for the winter.

They have an agent on hand in regards to that potential move, with icon Son recommending his South Korea team-mate for a move to north London.

Son is said to be playing a consulting role, noting Oh’s development and suitability for the Spurs side. Playing together for South Korea, in 16 games, Oh has assisted Son once.

Whether Tottenham will be able to land the striker in the winter is another question, though, as it’s believed Besiktas are reluctant to sanction a sale in January unless a lucrative offer is sent.

Oh Hyeon-gyu in sight in the Premier League

Spurs were linked with Oh ahead of the summer transfer window, as were Manchester United. That followed eight goals and four assists in 16 games for Besiktas in the second half of last season, following his mid-season move from Genk.

It was suggested in the Turkish media that the clubs were the main ones monitoring the Korean star.

In January of 2026, when Oh ended up joining Besiktas, he was also on the radar of a few Premier League sides.

TEAMtalk was aware that Fulham, Crystal Palace and Leeds were all pushing to land the South Korean striker.

It is not clear if any of those clubs retain their interest a year down the line, with Oh having scored only once this season after an explosion at Besiktas in the few months after he joined.

Tottenham Hotspur star Pedro Porro could reportedly be tempted by a move to Barcelona, despite the full-back recently signing a new long-term contract with the London club.

Porro, 27, penned a new deal running until 2031 back in June, and Spurs have the option to extend his contract by a further 12 months.

Roberto De Zerbi, who was appointed towards the end of last season, undoubtedly played a role in convincing Porro to commit his future to Tottenham.

However, things haven’t gone to plan since. The start to the current campaign has been a disaster for Spurs, who currently sit bottom of the table on two points after five matches.

According to Football Insider, Porro could be one of several Tottenham players ‘eyeing an exit’ if De Zerbi can’t turn his team’s form around quickly, and Barcelona are named as a potential option for him.

“It’s going to be interesting to see what happens with players like Pedro Porro,” a source told Football Insider.

“The key will be if Tottenham continue to struggle, because if they finish down the bottom of the table again, it’s going to be very hard to keep hold of their best players.

“He’s been happy at Tottenham, that’s why he signed a new contract in the summer, but if they keep finishing low down the table and they’re not in Europe, how long will that last?

“He’s on a long-term contract, but if Barcelona come calling, I think there is a very real chance that he could be tempted away.

“It would mean a move back to Spain, where he’s obviously very highly thought of after winning the World Cup, and maybe that’s something he would be interested in.

“As I say, I’m told he’s happy at Tottenham for now, but that might change if their results don’t improve quickly.”

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Pedro Porro could be tempted by LaLiga switch

It’s no secret that there has been interest from Spain in Porro, though Real Madrid have been linked more so than Barcelona in recent months. Madrid are believed to be long-term admirers of the Spanish international.

Barcelona, for their part, are currently well-stocked in the right-back position, with Joao Cancelo and Jules Kounde being Hansi Flick’s main options.

There is some uncertainty surrounding Kounde’s future, though.

TEAMtalk understands that Chelsea, who came close to signing Kounde back in 2022, could explore a move for the defender.

We revealed in an update earlier this week that Xabi Alonso is personally keen on a move for the French international.

A Kounde transfer away from Barcelona could therefore prompt the LaLiga side to make a move for Porro.

But for now, Tottenham are under no pressure to sell, and Porro will be focused on helping his team turn their dismal form around.

Tottenham Hotspur chief executive officer Vinai Venkatesham has given his full backing to under-pressure head coach Roberto De Zerbi, amid growing sack talk, while also delivering a key update on the club’s transfer business for 2027.

Having spent more than £300million on new signings over the summer, with 10 players walking through the door in total, Tottenham’s fortunes from the last two domestic campaigns have not improved through five games of the new campaign.

Indeed, the north London club currently sit rock-bottom of the Premier League table and also exited the Carabao Cup at the hands of Liverpool.

The club’s first two goals of the league season also came in the 3-2 loss to Aston Villa last time out, with the pressure mounting on De Zerbi after a winless start.

However, Venkatesham, speaking at a meeting with the club’s Fan Advisory Board at the Tottenham Hotspur Stadium recently, has reiterated his backing for the beleaguered boss.

“Vinai Venkatesham expressed confidence in Roberto De Zerbi, in the players brought in and in the changes made, noting the considerable work underway behind the scenes,” state the recently published minutes of the meeting.

“The club had made significant changes over the summer, both on and off the pitch, and recognised that these might take time to take full effect.

“Venkatesham was encouraged by aspects of the underlying performances since the opening day defeat, but acknowledged the disappointment at the current points total even at this early point in the season and recognised the frustration this caused supporters following the previous campaign.

“Supporter backing, home and away, had been excellent and was not taken for granted. He acknowledged that the club must earn supporters’ belief through results.”

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Venkatesham tempers hopes of further big-money Tottenham signings

Reacting to the club’s massive summer in the market, the minutes show that Venkatesham added: “The window had involved approximately 35 first-team transactions (incomings, outgoings and renewals).

“The squad had been strengthened with a focus on quality, character and physical robustness, combining Premier League experience with younger players able to develop with the club.

“The contract renewals of Micky van de Ven and Pedro Porro reflected the belief of two senior players in the club’s direction. The objective remained a squad able to compete at the level supporters expect.”

Venkatesham also made it clear that Tottenham must continue to sell players at the right time to stay in line with profit and sustainability rules in place with both the Premier League and UEFA, in a clear indication for fans not to expect any huge incomings in the upcoming January window – despite the club’s current predicament.

“Venkatesham explained that financial regulation represented a genuine constraint. The club had not recorded a profit since 2019, and its costs were rising through investment in the men’s team in wages and transfer fees,” read the meeting minutes.

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“He noted that successive 17th-place finishes and the absence of European revenue this season had also affected the club’s revenue position.

“The club monitored itself against the Premier League rules (squad cost of up to 85% of revenue). The UEFA rules are more restrictive – 70% of squad cost, together with a three-year profitability test – and remained relevant to the club’s ambition of returning to European competition.

“Venkatesham said that growing commercial income, including through concerts and other stadium events, was therefore important in creating additional capacity for football investment within the applicable financial rules. He reiterated that football remained the club’s clear priority.”

Tottenham are back in Premier League action on October 10, when they head to Manchester United in desperate search of their first three points of the campaign.