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Tottenham: Djed Spence informed of sale decision as Euro giants 'advance' on Spurs left

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'Advanced' talks for Tottenham left-back on as De Zerbi makes big Spence call - Football365
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Roberto De Zerbi has made his feelings clear on Djed Spence exiting Tottenham this summer, as a pair of European giants are in the mix for a Spurs left-back.

Spence’s future has changed a few times this summer. Our friends at TEAMtalk revealed he was told he wasn’t going to be part of De Zerbi’s plans going forward.

Amid the pursuit of Inter Milan, sources stated Spence was open to that move.

But that was before the World Cup, where the English defender put together some fantastic displays, particularly in the knockouts against Norway and Argentina.

De Zerbi has since told the versatile full-back he doesn’t want him to leave.

The Tottenham boss told media: “I repeat what I said to Djed, and to Lucas [Bergvall]

“I would like you to stay if you want to stay. If you don’t want to stay, if you want to leave, then you have to leave.”

Whether that changes Spence’s view on his future remains to be seen, but a lot of fans would surely like him to stay at Tottenham following his World Cup performances.

But there are a few side on his tail, with Liverpool and Everton also known to be admirers.

Souza agrees to Porto move

Fellow Tottenham left-back Souza appears to be nearing an exit from north London this summer, having only joined the club from Santos in January.

Indeed, GE Globo reports he has agreed to personal terms with Porto, who have been tracking the 20-year-old since his youth days.

Porto are now said to be in ‘advanced negotiations’ with Tottenham over the Brazilian, who is seeking regular opportunities as he looks to solidify himself for a spot in Brazil’s World Cup squad in four years.

READ: Double Tottenham exit ramps up as superstar helps one raid amid talks over similar move

Fellow Portuguese side Benfica are reported to have lodged a €20million (£17.1m) bid for Souza, and though it’s not clear what the outcome of that has been, it seems the fact Porto are in advanced negotiations means they’re on top.

Indeed, the giants are said to have ‘acted quickly’ to outbid their rivals.

With Souza having only played four times since joining Tottenham in January, it’s unlikely they’re married to the idea of keeping him, but the left-back’s future could be tied to that of Spence, as losing both would leave them short in the position.

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Marcus Rashford: Man Utd 'will accept' Tottenham '£30m offer' for 'shock move' as his transfer stance revealed

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Man Utd 'will accept' Tottenham '£30m offer' for Rashford as his exit stance revealed - Football365
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According to reports, Marcus Rashford could yet join Tottenham Hotspur from Manchester United this summer if they offer £30m to sign him.

Rashford‘s future remains uncertain heading into the 2026/27 campaign after Barcelona opted against signing him permanently from Man Utd.

The forward surpassed expectations during last season’s loan stint at the Nou Camp, having contributed 14 goals and 14 assists for the La Liga champions. Despite this, Barcelona have opted to buy Anthony Gordon instead this summer.

Therefore, it has been widely reported in recent months that Rashford is expected to return to Man Utd for pre-season after his post-World Cup break, and they could keep him instead of bringing in a new left winger.

READ: Every Premier League club’s transfer priority: Wingers for Arsenal, Liverpool as Chelsea fix problem position

It has also been reported that Man Utd boss Michael Carrick is happy to work with Rashford and vice-versa, but the club and player may still be leaning towards a transfer if the right opportunity arises.

Rashford’s huge wages are an issue for Man Utd, so they may prefer to get him off the books. While the player was intent on joining Barcelona permanently and could still prefer a move elsewhere.

Now, talkSPORT reporter Alex Crook claims Man Utd are ‘still expected’ to try to offload Rashford this summer, while he is ‘keen to leave’.

But with a move to Barcelona seemingly off the table, Rashford may have to accept a move to a Premier League rival, though Crook cannot see him joining Arsenal.

“I’m just not sure Marcus Rashford is a Mikel Arteta-type player,” Crook said on talkSPORT.

“If you look at what he’s done, and why Arsenal have been so successful in his tenure, he weeded out the sort of problematic characters from the dressing room, so I’m not sure that he would necessarily welcome Marcus Rashford with open arms.”

Marcus Rashford to Tottenham Hotspur?

Instead, Crook thinks Rashford could secure a ‘shock move’ to Tottenham because he can “see that deal happening”.

“I think if he goes anywhere in London, I’m keeping an eye on Tottenham,” Crook added.

“I could see that deal happening. Roberto De Zerbi believing that he can get the best out of Marcus Rashford.”

Crook continued: “When you say a cheap deal, I think probably an offer of £30million will be accepted by Manchester United, but you have to factor in he’s on £325,000 a week at Old Trafford, and doesn’t seem too willing to take a pay cut.”

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Tottenham pivot to signing Barcelona star after top target suffers serious injury

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The top striker target at Tottenham, Eli Junior Kroupi, has undergone surgery, with Spurs now pivoting towards signing a Barcelona frontman instead, according to reports.

Tottenham opened the chequebook nice and early this summer, getting big-money moves for Jan Paul van Hecke, Mateus Fernandes and Sandro Tonali over the line.

Roberto De Zerbi wants attacking reinforcements next, with both a winger and new striker on the agenda.

Manchester City’s Savinho is the No 1 prize for the wing positions. The latest on that developing story can be found here.

Up front, Tottenham’s top target had been Eli Junior Kroupi of Bournemouth, until now.

The wildly impressive Frenchman fractured his fifth metatarsal that has now required surgery to repair.

According to multiple respected sources including David Ornstein and Fabrizio Romano, the striker is expected to miss between three-four months while recovering.

Obviously, that has torpedoed Spurs’ ambitions of bringing Kroupi to north London this summer.

But according to our colleagues over on TEAMtalk, Tottenham have wasted no time identifying worthy replacements, and one in particular was in the headlines for all the right reasons this summer.

Tottenham want to sign Ferran Torres

Their insider, Graeme Bailey, revealed Barcelona and Spain striker, Ferran Torres, is a wanted man at Spurs.

Torres scored the winning goal for Spain in the 2026 World Cup final after helping Barcelona win LaLiga last term, though the next competitive fixture he plays might be for a different club.

The 26-year-old former Manchester City man only has one year remaining on his contract in Catalonia. PSG have been attempting to bring the Spaniard on board, and per Bailey, so too are Tottenham.

He explained: ‘Torres is set to available this summer should he fail to agree a new contract at Camp Nou and is a player Tottenham would relish the opportunity to pursue.

‘Paris Saint-Germain are currently advancing towards an agreement for Torres, but sources indicate that Spurs have already held discussions with intermediaries regarding the attacker’s situation and are keeping a close eye on developments.’

READ NEXT: Double Tottenham exit ramps up as superstar helps one raid amid talks over similar move

Taking to YouTube on Wednesday evening, Fabrizio Romano provided an update of his own on the versatile forward.

He insisted there’s “still nothing done or agreed” between Torres and PSG, though did sound a word of warning to Spurs and PSG when revealing Barcelona’s intention is to retain the player despite his contract situation.

The trusted reporter went on to note there’s nothing close with regards to Torres penning fresh terms at Barcelona.

Nevertheless, a new deal isn’t out of the question, and with Barca wanting to retain the player and Spurs facing heavyweight competition from PSG anyway, they face an uphill struggle when attempting to pull this one off.

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Tottenham pair en route to similar exits as superstar convinces international team

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Tottenham star convinced by international superstar to exit as team-mate in talks over similar move - Football365
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Two Tottenham stars look to be en route to similar locations, with Cristian Romero having spoken to an international team-mate about a move to Inter Milan.

When Romero planned to return to Argentina during Spurs’ relegation battle – and his own injury – last season, that seemed to confirm his plans for the next season. It has since been confirmed that he won’t be a Tottenham player for much longer.

Romero is nearing a move to Inter Milan, with only the conditions of the deal to go, with the clubs locked into talks, which are reportedly progressing well, and the defender already having agreed to personal terms.

Having discussed the potential move with Argentina team-mate Lautaro Martinez may have helped.

Indeed, Gazzetta dello Sport reveals the pair discussed the Inter deal during the post-World Cup break.

They state, as do other outlets, that all that we are waiting for is the terms of the move to be agreed.

Our friends at TEAMtalk have suggested while Tottenham wanted €50million (£42.8m), Inter have made a loan approach, with a deal nearer €40million (£34.3m) to follow, and the sides simply need to find a middle ground.

Vicario looks set to leave with Romero

Fellow senior Tottenham man Guglielmo Vicario also looks set to exit the north London club this summer.

Interest from both Juventus and Napoli in the £20million-rated goalkeeper has been evident for some time, and Football Insider now reports both are in club-to-club talks with Spurs over a move.

The Italian is said to be open to a return to Serie A, where he last played in 2022 with Empoli, while Tottenham are actively looking to sell him.

Both they and the two interested sides are keen on getting a deal over the line, so while it’s not clear yet which of the Italian clubs he’ll end up at, it seems that Vicario will indeed be leaving north London this summer.

Romero and Vicario have featured together in 90 matches, and have been two pillars of the club’s defence during their time there.

While losing both will mean losing two senior players, it must be said that the defence hasn’t been particularly solid of late and with the likes of Marcos Senesi, Jan Paul van Hecke and Andy Robertson signed, and Antonin Kinsky having impressed in net at the back end of the season, Tottenham might be coming out better by getting rid.

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Tottenham: 'Serious concern' over midfielder as Mateus Fernandes ACL rumour circles

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Mateus Fernandes injury update as 'serious concern' at Tottenham emerges - Football365
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Tottenham insider John Wenham has revealed “serious concern” over James Maddison, while a fellow insider has given an injury update on new midfielder Mateus Fernandes.

Spurs’ pre-season tour is taking place in New Zealand and Australia. They have so far won 1-0 and 2-0 against MK Dons and Auckland FC respectively, and will head to Australia to take on Sydney FC and then Chelsea.

In the first two games, there’s been no sign of Maddison, who returned from an ACL injury for the last three games of last season.

Tottenham Insider Wenham is concerned that he might not be fully right yet.

He told Tottenham News: “It is frustrating that James Maddison has gone on the tour, and not only in the first tour game against Auckland, but also the friendly against MK Dons, that he didn’t feature at all.

“Towards the back end of last season he was making a few appearances, I was hoping that this pre-season he’d be ready from the first game to be able to contribute, having had the whole summer off as well, building on his fitness, so I’m hopeful he will feature in these next few friendlies we’ve got out in Australia.

“If he doesn’t, then that is a serious concern.”

Fernandes injury update issued

Perhaps more concerning for Tottenham would be if £85million signing Fernandes was injured. Fans spotted him sitting out of a training session on tour and have made baseless claims that he’s done his own ACL.

However, football.london journalist Alasdair Gold has set the record straight on that.

He wrote: ‘The midfielder is not injured.

‘Instead, it is because head coach Roberto De Zerbi has been pushing the players hard in training, especially those who returned earlier to pre-season, and various players’ time in sessions and matches is being monitored and managed based on a variety of factors such as fatigue, little niggles, illness or even jet lag.

‘Various players have so far been rested from matches and training sessions with that in mind over the opening weeks of pre-season.

‘De Zerbi’s style of football is an all-action, draining one, and the players’ fitness is being pushed this summer to deal with that ahead of the season, with the arrival of the Italian’s long-time strength and conditioning coach Agostino Tibaudi to join another former colleague, first-team fitness coach Marcattilio Marcattilii, to ensure the team is ready for what is to come.’

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Tottenham set Man City deadline for Savinho deal as alternative winger targets lined up

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Tottenham Hotspur have reportedly told Manchester City they want a final answer on Savinho before the weekend or they will walk away from a potential £60million deal and pursue other targets instead.

It’s claimed that Spurs have informed City they do not want negotiations dragging into August and have set a clear deadline for the Premier League champions to make their decision.

Savinho has been Tottenham‘s priority left-wing target for the best part of a year, with the club failing to replace legendary former skipper Son Heung-min last summer.

Our friends over at TEAMtalk claim that Spurs actually agreed personal terms with the Brazil international ‘as far back as January’, when they came close to signing him before the move ultimately failed to materialise.

READ: Rogers to Chelsea only the third-biggest Premier League overpay so far this summer

A fresh report from the same source claims that while Tottenham spent much of the summer ‘assessing a range of attacking options’, they ‘always intended to return for Savinho’ and ‘did exactly that earlier this month’.

While Spurs actually made significant progress on a deal worth around £60m, negotiations have since stalled.

For their part, Man City initially made it clear they wanted to secure a replacement before sanctioning Savinho’s departure, while there have also been internal discussions over whether the 22-year-old should command a fee higher than Tottenham’s proposed package.

The TEAMtalk report has revealed how that delay has frustrated Tottenham, who have now set an ‘August 1 deadline to get the Savinho deal done and dusted’.

The report adds that the north London club have now ‘made it clear to both City and Savinho’s representatives that they want the transfer completed before August 1’, otherwise they will ‘switch their focus elsewhere’.

Savinho, meanwhile, is certainly his part to secure the switch, with a fresh report on Tuesday claiming that he has informed City that he wants out.

While Tottenham ‘remain optimistic that an agreement can still be reached’, club sources are said to stressed that their ‘deadline is genuine rather than a negotiating tactic’.

Tottenham also considering Savinho alternatives

While Spurs are determined not to allow one deal to hold up the rest of their summer business, they have identified alternative targets should City fail to give the green light to the Savinho deal.

Indeed, the likes of Antonio Nusa, Cody Gakpo, Rafael Leao and Jadon Sancho have all been assessed by transfer chiefs in north London.

READ NEXT: Transfer rumour ranking: Man Utd midfielder link makes no sense, two big Leeds deals

While confidence remains that Savinho will eventually become a Tottenham player, the coming days are now expected to prove decisive in what’s been a long-running transfer saga.

But unless City provide the clarity Spurs are demanding before the weekend, the north London club are prepared to end their pursuit and accelerate moves for other attacking options instead.

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Giant Tottenham signing coming after top target ‘informs’ club he’s leaving

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Tottenham have received a significant boost in their efforts to land their number one attacking target after he told his club he wants to go.

Tottenham spent heavily in the early phases of the summer transfer window, forking out a combined £237m on the triple signing of Jan Paul van Hecke, Mateus Fernandes and Sandro Tonali.

The clear need to add leadership and experience has also been solved through the arrivals of Martin Dubravka, Andy Robertson and Marcos Senesi.

Attention then turned to signing readymade forwards, though while clubs around them have been making moves, it’s all gone a bit quiet in north London.

It’s no secret Tottenham’s top target for the flanks is Manchester City’s Savinho. The player is well known to be open to joining Spurs, with the Brazilian eagerly awaiting for the two clubs to seal a deal.

And with progress slow, Fabrizio Romano has now revealed Savinho has taken matters into his own hands and attempted to give his potential switch to Tottenham a jolt.

Savinho informs Man City he wants out

Taking to X, Romano revealed Savinho has personally informed Man City of his express desire to leave the club this summer.

‘Savinho informs Manchester City about his desire to leave this summer,’ declared Romano.

‘Savinho wants to play more and develop in his career, #MCFC have been informed by the winger. All in Man City hands now.

‘Tottenham have Savinho on top of their list as revealed since May.’

Prior reports from the Daily Mail claimed Tottenham and Man City were discussing a transfer to the tune of around £60m.

At that price, Savinho would become Spurs’ fourth-most expensive ever signing, behind only Tonali (£100m), Fernandes (£85m) and Dominic Solanke (£65m add-ons included).

But as mentioned, updates on how the discussions were faring were in desperately short supply. With his actions on Tuesday, Savinho is clearly keen to see his future resolved sooner rather than later.

Over the weekend, transfer guru Fabrizio Romano revealed what he’s been hearing about Savinho’s proposed move to north London.

READ NEXT:Romano reveals how many more players Tottenham ‘will sign’ as one deal is ruled out

Roberto De Zerbi desperate to coach Savinho

He explained: “Then guys, let me mention for Tottenham, on Tottenham, the name of Savinho is the name I want to keep on the table because the coach, Roberto De Zerbi, said after midfield rebuild, after defence rebuild, now we need to do something upfront, we need important players, he said, we already have top players, well, so we need important players to add quality, not normal players.

“And when he says this, he means Savinho is one of the players they absolutely want. They remain in conversation for Savinho. Tottenham remain very keen for Savinho.

“So, Tottenham are on it for Savio, and the deal is absolutely on. And then we will see because they want to add one more. For sure, for Tottenham, there is going to be more movements, but at the moment, this is the situation around Savinho, considered a top target.

“They wait for Manchester City to tell them, okay, the player can leave, probably they wait for a replacement.

“Manchester City were trying for Diomande, as I told you, but Diomande is already off for Man City since a few days ago, and now the situation for Savinho remains on waiting for a green light from Manchester City.”

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Romano reveals how many more players Tottenham ‘will sign’ as one deal is ruled out

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Tottenham are not in the running to sign AC Milan winger Rafael Leao as Fabrizio Romano reveals how many more players they will sign.

Spurs have made a stunning start to the summer transfer window with the north London club moving fast to bring in six new signings so far.

After narrowly avoiding relegation to the Championship on the final day of last season, ENIC are doing everything in their power to make sure Roberto De Zerbi’s side don’t face a similar situation next term.

Andy Robertson, Marcos Senesi and Martin Dubravka all signed on free transfers, while Tottenham paid fees to bring in Mateus Fernandes, Sandro Tonali and Jan Paul van Hecke.

And now Tottenham’s attention has turned towards improving their frontline with speculation linking them to Milan’s Leao, Manchester City’s Savinho and Bournemouth’s Eli Junior Kroupi.

Italian transfer insider Romano has revealed that Tottenham will sign two more players with a deal for Portugal international Leao ruled out as Fenerbahce try to tie up a deal.

READ: Rogers to Chelsea only the third-biggest Premier League overpay so far this summer

Romano said on his YouTube channel: “According to my information, I told you several times there were rumours about Tottenham, [but] Rafa is not a target for Tottenham as of today.

“Should anything change I will let you know but as of today, the understanding is that Tottenham are not working on a deal for Rafael Leao, not at all, he is not a target.

“At the moment the target of Tottenham is Savinho [from Manchester City]. Tottenham want to sign Savinho and they will sign one more [player this summer] but at this stage, with Rafael Leao, the deal is not being discussed.

“There is a club attacking [the situation strongly] for Rafael Leao and that club is Fenerbahce. Fenerbahce travelled from Istanbul to Milano over the recent hours, Fenerbahce are there with a delegation and are working hard to sign Rafa Leao.”

Tottenham ‘remain very keen for Savinho’ – Romano

Bringing an update over the weekend specifically on Tottenham’s pursuit of Savinho, Romano said: “Then guys, let me mention for Tottenham, on Tottenham, the name of Savinho is the name I want to keep on the table because the coach, Roberto De Zerbi, said after midfield rebuild, after defence rebuild, now we need to do something upfront, we need important players, he said, we already have top players, well, so we need important players to add quality, not normal players.

READ: Top 10 veteran signings features Chelsea trio and Spurs, Liverpool cult heroes

“And when he says this, he means Savinho is one of the players they absolutely want. They remain in conversation for Savinho. Tottenham remain very keen for Savinho.

“So, Tottenham are on it for Savio, and the deal is absolutely on. And then we will see because they want to add one more. For sure, for Tottenham, there is going to be more movements, but at the moment, this is the situation around Savinho, considered a top target.

“They wait for Manchester City to tell them, okay, the player can leave, probably they wait for a replacement.

“Manchester City were trying for Diomande, as I told you, but Diomande is already off for Man City since a few days ago, and now the situation for Savinho remains on waiting for a green light from Manchester City.”

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Man Utd contact Tottenham for third midfield signing with £60m star ‘expected to leave’

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Man Utd have made contact with Tottenham over a potential deal to sign Sweden midfielder Lucas Bergvall this summer, according to reports.

The Red Devils have already got deals for two midfielders over the line with Youri Tielemans and Andrey Santos signing from Aston Villa and Chelsea respectively.

But Man Utd are looking to bring in a third midfielder in an effort to completely revamp Michael Carrick’s midfield ahead of the start of the season.

It had looked like Ederson would be the third midfield signing this summer but his deal from Atalanta collapsed due to medical issues.

Tottenham midfielder Bergvall, who was in and out of the side last season under three different managers, is set to leave Spurs this summer and is now reportedly attracting interest from Man Utd.

Fabrizio Romano recently explained that Bergvall is “expected to leave” as he doesn’t want to sit on the bench at Tottenham after the signings of Sandro Tonali and Mateus Fernandes.

READ: Top 10 veteran signings features Chelsea trio and Spurs, Liverpool cult heroes

Romano said on the Sweden international: “Lucas Bergvall from Tottenham is expected to leave the club this summer. Bergvall told Tottenham that he wants to play on a regular basis, he’s ready to maybe take a different step.

“But leaving Tottenham this summer is something that he has to do, according to the player, because he wants to play. And at Tottenham, the feeling of the boy after signing Mateus Fernandes, Sandro Tonali and they are not going to play European football, he doesn’t want to spend the season on bench or play ten minutes every two weeks.

“And so, for Bergvall, bid from Nottingham Forest and talks with Newcastle, both clubs are working for Lucas Bergvall. Both clubs are in contact, the highest proposal financially is from Nottingham Forest but Newcastle can offer a very competitive project and also ambitions, so there is a conversation ongoing with both clubs.

READ: Every Premier League club’s pre-season 2026 fixtures and results

“Let’s see what Bergvall decides to do but for sure the situation of Lucas Bergvall is one to watch in the next days because he is expected to leave Tottenham Hotspur.”

Man Utd make their move for Bergvall

There have been reports that Brighton are willing to match Tottenham’s £60m price tag for Bergvall, while there is also interest from Nottingham Forest.

However, a popular transfer account on X with over 700k followers has revealed that Man Utd have made contact over a move for Bergvall.

The account wrote: ‘Exclusive. Manchester United is making some intriguing moves today in the transfer market. Our sources have revealed that they’ve reached out to Tottenham regarding midfielder Lucas Bergvall. Spurs have reportedly set his price tag at around the £50m-£55m mark.’

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Chelsea dominate Premier League top ten as new transfer obsession restored

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Chelsea have three players in the top five Premier League signings over the age of 30 – and it could have been more.

Thiago Silva and Gianluca Vialli can consider themselves unfortunate not to make the top 10 veteran signings as Chelsea rediscover their appetite for an oldie.

The criteria here: Premier League era; 30 or over when they signed; and outfield players only.

The summer of 1997 saw Italy international Lombardo swap Juventus, with whom he’d just won the Serie A title, for Palace, who’d just won the play-offs to get back in the Premier League.

“He’s a top international player who is very flexible and will give us that little bit of class, that little bit of guile, we may have been missing,” said manager Steve Coppell, unveiling Lombardo a week before the start of the season which opened with the 31-year-old scoring on his debut in a win at Everton.

That was a sign of things to come for Lombardo, if not Palace. The new boy became a cult hero among fans and team-mates, who recognised they were barely worthy of sharing the same pitch. Even with Lombardo, though, Palace struggled.

In March, Coppell moved upstairs, making way for Lombardo to take over as manager, assisted by Thomas Brolin. The Italian failed to save Palace from the drop, but so enamoured was he by the Eagles, he stuck around for half a season in the second tier too.

MORE: Remembering Attilio Lombardo’s bizarre 18 months at Crystal Palace

Gerard Houllier had to win over a sceptical fanbase, dressing room and assistant manager when he moved for 35-year-old McAllister when the midfielder’s Coventry contract expired in 2000.

Houllier’s right-hand man Phil Thompson thought signing the veteran “sent the wrong message”, while Steven Gerrard was fuming.

‘How wrong I was,’ wrote Gerrard in his autobiography. ‘Meeting this intelligent Scot was an important moment in my career. As a midfielder and a man, Gary Mac was special.’

That was evident in two seasons at Anfield in which he served as the young team’s elder statesman, bringing class and composure to Houllier’s midfield, helping the Reds to a treble and the Champions League.

Many of the players on this list played in an era when footballers weren’t condemned to the knacker’s yard on their 30th birthday. But Xhaka is furthering the modern-day veterans’ cause having been last term’s signing of the season.

“He’s the most influential signing in the North East since Kevin Keegan at Newcastle in 1982,” North East scribe Ian Murtagh told the BBC and he’s not exaggerating. Xhaka not only pulled the Sunderland strings on the pitch but also set the example off it for the 427 other new arrivals last season.

Xhaka, 32 when he signed, was more influential than any other player in helping Sunderland not only defy expectations of relegation but secure European football for the first time in more than half a century. So much so, he was the first veteran Chelsea wanted to sign this summer. Just not enough to make a bid worth considering.

A few eyebrows were raised when Manchester United moved to replace the retiring Eric Cantona, 30, with Sheringham, 31, in the summer of 2007. And the doubters looked for a while to have been right.

Sheringham started slowly at Old Trafford. In his first season, as he was reminded at away grounds across the country, he won f*** all. His second campaign didn’t seem to be going much better up until the England striker helped United win the lot.

Even after that, in his third season, Sheringham’s opportunities were limited as Dwight Yorke and Andy Cole formed one of the game’s most lethal strike partnerships. But in 2000/01, aged 35, Sheringham saved his best season for last, proving pivotal in a third consecutive league title, top-scoring while winning the FWA and PFA Player of the Year awards.

Back in 2003, Sam Allardyce was viewed as a visionary. The Bolton manager, together with his staff, took the Trotters from the Championship to Europe while recruiting World Cup winners and Champions League stars to play alongside less-heralded names like Mike Whitlow, Anthony Barness and Simon Charlton.

Djorkaeff, approaching 34, was the first star name through the door at The Reebok. While Bolton were yo-yoing between divisions with a squad similar to that which earned promotion through the play-offs in 2001, Allardyce met the France star for dinner and pints of wine in Germany, where he was in the midst of an unhappy spell with Kaiserslautern. Big Sam sold Djorkaeff on the idea of half a season in Lancashire, scrapping at the foot of the Premier League.

When the former Inter and PSG star helped Bolton survive, Djorkaeff committed for two more years, prompting other big names like Jay-Jay Okocha, Ivan Campo, Fernando Hierro and Nicolas Anelka to follow in his footsteps. But Djokaeff was the one who got the Bolton ball rolling.

“We will not miss Makelele,” said Florentino Perez when he sold 30-year-old Makelele to a Chelsea recently bought by Roman Abramovich. “His technique is average, he lacks the speed and skill to take the ball past opponents, and 90% of his distribution either goes backwards or sideways. He wasn’t a header of the ball and he rarely passed the ball more than three metres. Younger players will arrive who will cause Makelele to be forgotten.”

It was hardly the first or last of Perez’s bad takes, but nor was it a coincidence that in the five seasons Makelele played for Chelsea, they won two Premier League titles, an FA Cup and two League Cups, while Real Madrid won nothing.

The France midfielder was first the “battery” in Claudio Ranieri’s Chelsea before becoming the most important player in Jose Mourinho’s all-conquering Blues team while mastering his position to the extent it was named after him.

”You will all have your opinions,” said Harry Redknapp in response to criticism for signing Di Canio for West Ham in January 1999. ”But in the end I’ll be right.”

He was. Di Canio was a bold signing given his checkered past. He hadn’t played since an 11-game ban for shoving a referee and was sold by Sheffield Wednesday while AWOL. Redknapp had to convince his own chairman that it wasn’t a terrible idea.

Di Canio repaid Redknapp’s faith in spades over four and half seasons in east London. The Italian hot-head became a hero at Upton Park – especially so when he turned down Manchester United in 2002-02.

Some may have thought the Ballon d’Or winner was coming for the money when he signed for mid-table Chelsea from AC Milan shortly before his 33rd birthday. But Gullit changed Chelsea and the Premier League too.

The Netherlands star was recruited by Glenn Hoddle initially to play as a sweeper, despite his success as an attacking midfielder in Milan. But his class confused team-mates as well as opponents.

“It was like watching an 18-year-old play among 12-year-olds,” said Hoddle, who moved Gullit into midfield after watching his other Chelsea players struggle to keep up. Gullit finished the 1995-96 season as player of the season runner-up to Eric Cantona before replacing Hoddle as player-manager, ending their 26-year trophy drought in his first season in charge. He also signed two other players on this list.

Klinsmann was three weeks into his 30s when he signed for Spurs aboard Alan Sugar’s Monaco-moored yacht. Sugar paid £2million for “one of the best players in the world” as manager Ossie Ardiles described the Germany striker, who had just scored five goals at the 1994 World Cup.

Klinsmann proved the manager right with 30 goals in all competitions – Ardiles only saw 12 before he was sacked – including 20 in the Premier League, the first of which was followed by a self-deprecating dive at Hillsborough which became one of the Premier League’s most iconic celebrations.

The German ended the only season of his first Spurs spell – he returned in 1997/98 – as the first player ever to win the FWA Player of the Year in his first season in England, was selected in the PFA Team of the Year and ended 1995 as the Ballon d’Or runner-up.

MORE: How Jurgen Klinsmann at Spurs changed English football forever

Chelsea’s greatest ever player?

Zola was 30 when he signed from Parma in November 1996. Despite missing the first three months of the season and it being assumed the tiny technician would take time to acclimatise to the Premier League, the Italian still won the 1997 FWA Player of the Year award.

And he maintained those ridiculously high standards for another six seasons, scoring 80 goals in 312 appearances while helping to transform Chelsea from mid-table also-rans to a club regularly competing for the domestic and European honours.

Zola’s impact went way beyond silverware and stats. He was adored at the Bridge and admired far beyond for making the game as fun to watch as he had playing it.

‘Little Gianfranco Zola, he annoyed me. He was one of these players who were unperturbed about who he was playing against. He always seemed to have a smile on his face and that annoyed me. How can he be enjoying himself playing against United? Nobody else does. He was a fantastic player and I loved watching him. It was enjoyable and for me to say that about an opponent tells you how much I admired him.’

Sir Alex Ferguson

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