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Tottenham have already been extremely busy this transfer window with Roberto De Zerbi preparing his squad for the upcoming Premier League season

Tottenham have broken their transfer record twice already this summer as they aim to bounce back from a majorly disappointing 2025/26 season.

The Spurs midfield has been totally transformed with the signings of Sandro Tonali and Mateus Fernandes for a combined fee of £185million. Roberto De Zerbi had smashed the club's transfer record with Fernandes' signing for £85m last week, before splashing an initial £92.5m plus £7.5m in add-ons for the Newcastle star.

That might not be the end of the spending either, with more big money moves in the pipeline. However, Spurs have also utilised the free agent market, having completed shrewd deals for Andy Robertson, Marcos Senesi and Martin Dubravka, after the expiry of their contracts at previous clubs.

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De Zerbi could continue in this vein of spending and saving big with high-profile signings and cheeky free agent deals to balance the budget. Here, football.london examines three former free agent signings and how they performed for the Lilywhites.

Teddy Sheringham

Teddy Sheringham wasn't initially a free transfer to Spurs; he signed his first contract with the club from Nottingham Forest for around £2.1m in 1992. He stamped his authority on the Premier League during his time in north London and became a prolific striker - but his lack of major honours pushed through a £3.5m move to Manchester United in 1997.

Here, Sheringham would complete the coveted Treble by clinching the Premier League, FA Cup and winning the Champions League in dramatic fashion against Bayern Munich. The England international scored one and set up another as United beat the German side in the dying minutes.

He continued excellent form at Old Trafford, winning more trophies and then returned to north London on a free transfer by 2001. Throughout his Spurs career, Sheringham made 277 appearances and scored 125 goals, as well as contributing 53 assists.

Stats show that the former striker played the majority of his career with Tottenham and was inducted into the club's Hall of Fame alongside Clive Allen in 2008 - the same year he stepped down from professional football.

William Gallas

William Gallas is a curious case in Premier League history, having played for three of London's biggest clubs one after the other. He started his career in England at Chelsea, signing for £6.2m in 2001 before moving to Arsenal by 2006.

Gallas would go on to become the Gunners captain for a period before tensions saw him replaced by Cesc Fabregas as the man with the armband. His contract expired with Arsenal in 2010 and he would make the short trip to sign for Spurs on a free.

The defender made 78 appearances for the Lilywhites, scoring one goal and seeing out the rest of his Premier League career. Gallas would depart Spurs in 2013 and became the first Frenchman to play in the Australian league when he signed for Perth Glory in October.

He retired that same year at the age of 37 after winning two Premier League titles and two domestic cups - all of these with the Blues.

Edgar Davids

Edgar Davids had a short but sweet tenure in the Premier League with Tottenham, spending two seasons in north London. The Dutch midfielder had already earned the 'world-class' tag from his time with Juventus, where he made his presence known both for club and country.

Between 1997 and 2004, Davids won three Serie A titles, a host of domestic cups and was part of the Netherlands squad that finished fourth in the World Cup and third in two European Championships. He racked up 235 appearances for Juve and made 32 goal contributions.

He would have stints at Barcelona and Inter Milan before joining Spurs on a free transfer in 2005. He would only make three goal contributions in 44 appearances for the club but continues to hold a soft spot in his heart for the Lilywhites.

Speaking before a friendly between two of his former clubs - Juve and Spurs - in 2017, Davids said: "It’s no coincidence that everything is coming together and you’ve had the last couple of unbelievable seasons in the Premier League. It’s not a one-off. Spurs are at that level and that’s why I’m so proud of the club. Spurs have created that culture.

"I like this team a lot. When I see this team play I see fun, I see youth, enthusiasm, football on the edge, fun football. They have fun and they are big, big talents. How can you not love this team?"

Tottenham Hotspur are among the Premier League clubs that have an interest in the talented young Bournemouth attacker

Spending mega money on Eli Junior Kroupi will not provide Tottenham with a ready-made striker, believes ex-Tottenham and France forward Louis Saha.

The France U21 international scored 13 goals in the Premier League last season as a teenager, including one against Spurs, and he only turned 20 last month. The north London club have been linked with continuing their £237million transfer spend so far this summer with a big bid for the £85million-plus rated Kroupi.

Most of the Premier League's big clubs, including champions Arsenal, hold an interest in Kroupi, as do some of Europe's top sides, and Bournemouth are currently putting a 'not for sale' sign on the attacker.

Former Manchester United striker Saha believes his young compatriot has plenty of talent but would not arrive as the ready-made star for Roberto De Zerbi that such a huge transfer would normally guarantee.

"Eli Kroupi Jr has had a phenomenal season for Bournemouth, so I’m not surprised there’s interest from Spurs in him. One of the great things about Kroupi Jr is that he scored 13 Premier League goals when rarely playing 90 minutes. That shows he has got quality, adaptation, and he can clearly impact a game from the bench.

"However, this is what worries me about him if Spurs spend big money on him this summer. You can’t question his talent, but at such a young age, is he going to be able to play every game next season, work hard and manage 90 minutes? That’s what you want from a new big-money striker that comes into the club," Saha said in association with LiveFootballTickets.

"I’m not saying he can’t do it, but he had his minutes managed really well by Andoni Iraola at Bournemouth last season. Spurs have had plenty of attackers of a similar brand to Kroupi Jr over the past few years. Strikers who are quick, versatile, can link up play and score a few goals. But what they need now is a striker to come in, gel with their current wingers and new signings who will score 20 or 25 goals in the Premier League next season, and I’m not sure Kroupi Jr is that guy. If he was that player, he’d have made the France squad for the World Cup this summer."

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Saha is expecting big things though from Tottenham after their midfield signings of £100million Sandro Tonali and £85million Mateus Fernandes from Newcastle and West Ham respectively.

"I think a midfield of Tonali, Fernandes and James Maddison will be fantastic next season, one of the best in the league. Over the past few years, Spurs have always had players of good quality but have struggled getting them to gel for a full 90 minutes of a football game," said the Frenchman.

"Spurs need to ensure they are maintaining tempo and quality throughout games. They can’t let teams overwhelm them as easily as they did last season. Spurs have signed Marcos Senesi and Jan Paul van Hecke, which will help them with this. However, I still feel like they need more signings in forward areas if they are going to be competing for trophies next season."

He added: "With the money Spurs are spending this summer, the Champions League is exactly what they are aiming for and will be expecting of Roberto De Zerbi and his players. They are making a statement, spending hundreds of millions and signing good free agents, they are assembling a team to compete with the very best in world football.

"Spurs have the best infrastructure of any club in world football, and it looks like they are now intending on competing with the very best. They have signed some terrific players, and they will only play one game a week for the majority of next season. Therefore, I expect them to qualify for the Champions League easily next season."

The Tottenham Hotspur captain has been in the headlines again this week after a match-deciding performance at the World Cup

Argentina boss Lionel Scaloni once admitted what Tottenham managers have always known - there's no point trying to control Cristian Romero.

The Spurs captain is a force of nature on a football pitch, whether that's when he's crunching into tackles or when the centre-back wanders up the pitch and decides to become a striker for a spell. The 28-year-old has done the latter to major effect over the years for the north London club and last season recorded 10 goal involvements from 32 matches despite being a central defender.

Romero crucially did it for his country with the headed goal that kickstarted Argentina's dramatic late comeback against Egypt at the World Cup on Tuesday night in Atlanta. After Enzo Fernandez then scored the winner in stoppage time, rather than rushing over to the Chelsea man, the Spurs defender instead celebrated wildly by punching the air repeatedly in the path of Mohamed Salah, who had to step around him, with goalkeeper Emiliano Martinez grabbing Romero to ensure he did not spark a reaction from the Egyptian players.

Romero had done similar in the face of Kylian Mbappe after Lionel Messi's extra-time goal in the World Cup final in Qatar, with the Frenchman not flinching. It's a reaction Spurs fans have also seen over the years in club matches, including celebrating in Harry Maguire's face after the Manchester United defender scored an own goal against the north London outfit.

The Tottenham skipper, who arrived at this World Cup after suffering a knee injury which ended his Premier League season prematurely, had also forced the Diney Borges own goal with his extra-time header to break Cape Verde hearts in the last 32.

Romero drew plenty of praise back home for his performance against Egypt with Argentine newspaper La Nacion, translated by Sport Witness, saying that the Spurs man "defends as a marshal and finishes as a number nine".

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The media outlet, when speaking about Romero's goal against Egypt, referenced some previous quotes from his international boss Scaloni about the defender's forays forward and those words confirmed a truth that many Spurs head coaches have felt the same way about.

"Sometimes we tell Cuti not to go up, but he goes anyway, it’s in his genes. He made a run like when he was at Atalanta. He has that raw talent that you can't control, and sometimes it pays off for us," said Scaloni.

Messi, who scored Argentina's second goal against Egypt, once called Romero "the best defender in the world" and said that "it puts my mind at ease knowing Cuti's back there, I don't have to turn around to look".

Romero's future at Spurs remains unclear this summer. With Roberto De Zerbi pushing for the arrivals of Romero's Argentina team-mate Marcos Senesi and his former Brighton centre-back Jan Paul van Hecke, Romero could depart as Radu Dragusin has done to Fiorentina this week.

Romero has had long-time interest from Atletico Madrid and Messi's old side Barcelona are also reportedly considering a move. The problem could be Tottenham's price tag for a player starring at the World Cup, with three years left on his contract.

Spurs have just signed Van Hecke for £52million despite only having 12 months left on his deal at Brighton, before selling 19-year-old Luka Vuskovic for £50million despite the teenager having never played a competitive game for the club.

Romero's price tag should logically be higher and will only increase with each passing game-changing performance at the World Cup.

The young midfielder made his feelings clear after Tottenham Hotspur let one of their players depart in the transfer window

Archie Gray posted a heartfelt farewell to Radu Dragusin after the Romanian left Tottenham to head to Serie A side Fiorentina.

The Italian side agreed a loan with an obligation to buy Dragusin which could be worth as much as £21.4million (25m euros) if the centre-back plays a set amount of games. Spurs will also hold a 10 per cent sell-on clause on any profit Fiorentina should make on the 24-year-old with a later sale.

The former Genoa and Juventus defender played 48 times for the north London club around an 11 month absence in 2025 from competitive action due to an anterior cruciate ligament injury. However, he has become surplus to requirements with Tottenham signing Jan Paul van Hecke and Marcos Senesi for head coach Roberto De Zerbi.

Now Dragusin will reunite with former Spurs sporting director Fabio Paratici who has been involved in every transfer in his senior career so far with the Italian now at Fiorentina.

The Romania international started most of Tottenham's group stage games on their way to winning the Europa League in the 2024/25 season before suffering that ACL tear in the final match of the group against Elfsborg in January last year.

Now he will head back to Serie A after making a big impact on young midfielder Gray and a number of his team-mates.

Gray posted a photo of the two players embracing in an Instagram Story upload with the caption, along with crying and heart emojis: "Gonna miss u brother. All the best Radu Dragusin."

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Dragusin himself had posted a touching and heartfelt goodbye on social media to the club and supporters as he departed for Fiorentina.

"Some chapters become part of who you are. From the day I arrived at Tottenham, I was proud to wear this badge, and looking back, I’m grateful for all the memories I made at this club," wrote the Romanian.

"Lifting the Europa League trophy is something I’ll always be proud of. Sharing that moment with my teammates, the staff and our supporters is a memory I’ll carry with me forever.

"But football isn’t only about the moments you celebrate. It’s also about the moments that test you the most. During the toughest period of my career, when injury kept me off the pitch, I never felt alone. The support I received from this club, my teammates and the incredible Spurs fans gave me strength every single day.

"Tottenham has helped me grow, not only as a footballer, but as a person. Thank you to everyone at the club for your trust and support. And thank you to every supporter for always being there. Your passion, loyalty and support have meant so much to me.

"As I take the next step in my career, I do so with nothing but gratitude and respect. Thank you, Spurs."

The post was responded to by various first team players such as Micky van de Ven, Destiny Udogie and Dominic Solanke with blue hearts and liked by many more such as James Maddison and Guglielmo Vicario with Dragusin having left an impression on his team-mates.

Tottenham's £185million midfield duo are set to bolster Roberto De Zerbi's ranks and quickly join pre-season training with their new team-mates

Roberto De Zerbi will quickly be able to start working with his new signings Sandro Tonali and Mateus Fernandes as Tottenham's pre-season begins.

Spurs snapped up the duo for a combined £185million with Fernandes costing £85million from West Ham and Tonali potentially becoming the north London club's first £100million player if the £7.5million in add-ons are activated on top of the £92.5million fee paid to Newcastle.

As well as their obvious midfield ability, another benefit of signing the duo is that neither were involved in the World Cup this summer across the Atlantic which means that they can get started quickly with De Zerbi and his coaching staff for pre-season training, to learn the Italian's ways at Hotspur Way.

football.london understands that Fernandes is set to be part of the group of players who will arrive first at the club's Enfield training complex from this Friday for medical and physical testing and gym work. They will then begin full sessions on the training pitches with and the coaching staff from Monday.

Tonali will also be involved from Friday, but only if his work permit is finalised following his move to the club this week.

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Others involved in the early days of pre-season will be James Maddison and Dominic Solanke along with new signing Martin Dubravka, Conor Gallagher, Archie Gray, Richarlison, Mathys Tel, Destiny Udogie, Ben Davies, Souza, Antonin Kinsky, Guglielmo Vicario and Brandon Austin and younger players such as Mikey Moore, Will Lankshear and Jamie Donley, Yang Min-hyeok and Kota Takai.

Mohammed Kudus and Dejan Kulusevski will be involved when they are fit to return from the long-term injuries that dashed their World Cup hopes, while Wilson Odobert and Xavi Simons will not be back until the turn of the year from their ACL injuries.

Tottenham had 12 players away at the World Cup in Cristian Romero, Kevin Danso, Luka Vuskovic, Djed Spence, Pape Matar Sarr, Pedro Porro, Lucas Bergvall, Micky van de Ven and Rodrigo Bentancur as well as summer signings Andy Robertson, Marcos Senesi and Jan Paul van Hecke.

Only Romero, Senesi, Spence and Porro remain with Robertson and Bentancur likely to be the first back to pre-season this month from the international group after their exits with Scotland and Uruguay respectively in the group stages. All players will get offered at least three weeks of rest after their involvement at the tournament ends.

The first summer friendly at the moment involves Tottenham hosting League One side MK Dons at Hotspur Way on Wednesday, July 22 before the club heads off on its tour to New Zealand and Australia.

The Tottenham wonderkid has sent a heartfelt transfer message to Alfie Devine

Mikey Moore has sent a four-word message to Alfie Devine after the midfielder's permanent exit from Tottenham Hotspur was confirmed. The 21-year-old, who joined Spurs from Wigan Athletic in July 2020, has completed a move to Preston North End after a successful loan spell at the Championship side last season.

Devine scored eight goals and managed eight assists in 48 appearances for the Lancashire club last campaign. He impressed so much that Preston exercised their option to buy the midfielder for around £6million, which will be paid in instalments.

Upon leaving Tottenham Hotspur Stadium, Devine said: "My time at this club has come to an end after 6 years of memories, experience and learning. Huge thanks to everyone involved with my time here and something I’ll cherish forever, thank you."

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The post on Instagram has been liked more than 16,000 times with hundreds more taking to the comments to thank Devine for his time at the club and wish him well for the future. Mikey Moore was among those to comment, writing: "All the best bro."

Tottenham youngster Dane Scarlett commented three love heart emojis and Alfie Dorrington commented a similar message. Luca Gunter, who last week joined Boreham Wood on loan until the end of the season, wrote: "All the best."

While Devine's time at Tottenham has come to an end, Spurs boss Roberto De Zerbi wants to take a close look at Moore in pre-season this summer with the club not interested in letting the teenager leave permanently, football.london understands.

The 18-year-old academy product played 47 times for Rangers last season and his impressive performances helped him pick up both the PFA Scotland Premiership Young Player of the Year and Rangers' Young Player of the Year awards.

football.london understands that Spurs are not interested in selling Moore this summer despite clubs circling amid the squad overhaul currently being undertaken in north London. It's understood De Zerbi wants to take a closer look at the talented teen in pre-season when the players return to Hotspur Way on Friday, July 10.

The Italian will then make the decision whether to keep the youngster involved in his first team set-up for the first half of the season or if with the lack of fixtures ahead at Tottenham, due to the absence of European football, it is better to allow him another loan spell elsewhere to ensure he starts week in, week out to continue the developmental strides he made north of the border if the perfect offer comes in.

Speaking on his future, Moore said: "There's a new manager at Spurs at the minute and obviously I'm a Spurs player, so we'll have to see what he says about me, what he wants me to do, what the people around me want me to do. I think that's all I can say at the moment. I'm going to go back there and see what the new people say in the building and from there I'll make a decision."

Preston North End have signed Alfie Devine from Tottenham in a deal worth around £6million

Alfie Devine has posted an emotional goodbye message on social media after his exit from Tottenham Hotspur was confirmed.

The 21-year-old has joined Preston North End in a permanent deal after the midfielder enjoyed a successful loan spell with the Championship side last season. As part of that loan deal, Preston agreed an option with Tottenham to buy the England U20 star in a deal worth around £6million.

That figure is more than twice their transfer record but the youngster impressed so much that the Lancashire club, who finished 14th in the Championship last season, were said by the local Preston media to have triggered the option with payments in instalments.

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Devine's exit from Spurs was confirmed on Tuesday and the midfielder, who had just 12 months left on his contract at the Lilywhites, has taken to social media to post a goodbye message.

The player wrote: "My time at this club has come to an end after 6 years of memories, experience and learning. Huge thanks to everyone involved with my time here and something I’ll cherish forever, thank you."

Devine is Tottenham's youngest ever goalscorer after his FA Cup strike in 2021 as a 16-year-old against Marine, but two appearances in that competition are the only occasions in which he has pulled on a Spurs shirt in senior competitive matches.

He will now ply his trade in the Championship with Preston, where he contributed eight goals and eight assists in 48 appearances last season. When asked what he wants to achieve at Preston upon completing the move, he said: "Big things.

“I think that's one of the things that I want as a player and I'm sure everyone wants as a player. You want to go on, win things, get promotion and I think that this is a perfect club to go and do that.

“That's why I decided to come back. I feel like there's a real good feeling about the place. We showed last year what we're capable of doing and that's one of the reasons why I've come back here, because I feel like we can hopefully do that all the way throughout the season and achieve something good.”

The Tottenham starlet has been told to stay at the north London club by a compatriot who has plenty of experience in the area

Lucas Bergvall should remain at Tottenham and not complain about his situation, believes former Arsenal and Sweden star Anders Limpar.

The 20-year-old midfielder informed Spurs that he wanted a fresh challenge this summer as minutes look hard to come by for him this coming season under Roberto De Zerbi. That's because the north London club have spent £185million on Mateus Fernandes and Sandro Tonali to bolster their midfield.

Tottenham are not looking to sell Bergvall this summer and believe he will get minutes this season, but that has not stopped interest from numerous clubs, with Nottingham Forest among the Swede's suitors after his World Cup exploits. The young midfielder has played 78 games for the Premier League club across his first two seasons in N17 after Tottenham saw off Barcelona to sign him in 2024.

Limpar, who came through the academy of Brommapojkarna like the Spurs youngster, does not like the way the midfielder has gone about things despite his own leanings after four years spent across north London at the Gunners.

"First of all, I don't like when a player who's struggling with his team, and a new manager comes in, the player straight away complains and wants to leave. I don't like that because you have to work yourself back into the team and not just say in the press that I want to leave. I don't like that," the 60-year-old told Rekatochklart.

"Lucas Bergvall is a very, very good player. You can see he has a big heart as well. He doesn't let the team down. He was one of the guys who worked [against France] all the way until he got subbed.

"I don't like that he wants to leave. It's better for the Swedes to stay at Tottenham and make them great again. That's a bigger value for me."

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Limpar added: "He can probably choose from three or four clubs now, if he stays in the Premier League. We'll have to wait and see but yet again, he can play for a good side. Lot of talk about him going to Liverpool.

"It's too easy to say 'I want to leave'. When a player's on the bench, it's always the manager's fault, the crowd's fault. You have to look at yourself and dig in. I don't like players who just suddenly find everything wrong with the club and want to leave, rather than putting their fist to their hand, working hard and talking to the manager to understand where they can improve. I would have liked to see that here.

"He's at a time and place in his career where he should stay humble towards his club, but if it goes that way that he's swapping clubs, then all the best to Lucas. He's in my heart. He's like Benjamin Nygren who plays with heart. He's not a player who hides himself when the result is not going his way. He wants to do something on the pitch. I like him a lot."

Tottenham Hotspur have announced the departure of Alfie Devine who has joined Preston North End on a permanent deal

Tottenham Hotspur have confirmed the departure of midfielder Alfie Devine on a permanent deal. Spurs have announced that the 21-year-old has completed a move to Preston North End, seeing his time in north London officially come to an end.

Devine spent last season on loan at Preston, during which time he made 48 appearances for the Championship club across all competitions.

It was thanks to those appearances that Devine earned the Young Player of the Year award at Preston, and he has now completed a move to Deepdale on a permanent basis.

Preston had the option of signing Devine on a permanent transfer following the conclusion of his loan spell, with the Lilywhites now exercising that option and have officially signed the Spurs midfielder.

As reported by football.london earlier on Tuesday, Devine was set to undergo a medical to leave Tottenham on a permanent basis, with the green light given to the move with the midfielder having just 12 months remaining on his contract.

Devine scored eight goals during his loan spell at Preston and has now expressed his delight at making his move to Deepdale permanent, admitting that a departure from Spurs was often on his mind.

“From the end of last season going into the summer, it was always a priority in terms of where I wanted to be. It took its time, but I'm delighted it's gone through,” Devine told Preston’s club website.

“From the first minute I came here until my last minute of last season, I absolutely loved it. The fans, staff, players, everyone around the place made me feel so welcome.”

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Preston also confirmed that the move for Devine represents a club-record fee for the Championship outfit, with the midfielder putting pen to paper on a five-year deal.

Devine was managed by Preston boss Paul Heckingbottom, and the Lilywhites manager has outlined why he was keen to bring the now-former Tottenham star back to Deepdale.

“I’m really pleased to get it over the line,” Heckingbottom said.

“A lot of people have worked hard at it, and Alfie made no secret of the fact that he enjoyed his time here and wanted to play here.

“We think that it's good business, not only in the short term and helping us get results on the pitch, but it's also really good business for the football club as well.”

Cristian Romero was a key player for Argentina in their dramatic 3-2 win over Egypt in the last-16 of the World Cup, with the Tottenham Hotspur defender on the score sheet

Manchester United legend Roy Keane was quick to deliver praise to Tottenham Hotspur defender Cristian Romero after his goal for Argentina at the World Cup.

Argentina overturned a two-goal deficit late in the second period to claim a 3-2 triumph over Egypt in the last-16 encounter at the World Cup, with Romero, Lionel Messi and Enzo Fernandez finding the back of the net.

Romero featured in the backline alongside Lisandro Martinez for Argentina and was instrumental in keeping his nation's aspirations of retaining their title alive.

Keane was joined by Gary Neville in the ITV studio, offering his praise for Romero following the Tottenham defender's goal against Egypt.

"It's his movement,” Keane said. “It's obviously a brilliant delivery. His movement is like a striker, he just peels off the back of the defender.

“Yes, it's poor defending, they're trying to hold a high line. But his movement and his timing is like a top-class striker. Absolutely fantastic. We go back to that desire to try and get back in the game."

Neville also referenced the performances of both Romero and Martinez as he praised the mentality the Argentina players have to be able to recover from a two-goal deficit in Atlanta.

"You watch [Cristian] Romero and [Lisandro] Martinez, and they're the best 'worst centre-halves' in the world,” Neville remarked during ITV’s post-match coverage.

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“You watch them, they give goals away constantly. But they don't care about giving goals away because they'll score goals at the other end. They have massive personalities and they keep going.

"Look, at that point in the game, you think Argentina are hanging on for dear life. They're fighting for their lives and Romero is part of that comeback, you know what I mean? Why is he there?

“You always ask the questions: 'why is Martinez scoring in the last game? Why is Romero scoring there?' Because they don't give in and they fight, and they fight, and they fight."