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Tottenham Hotspur were making sharp progress under Mauricio Pochettino when the Argentine became manager in 2014, with a Premier League title challenge and Champions League final appearance following in the years after his arrival.

One player who proved imperative to Spurs during that period under Pochettino was Dele, who signed for the club for £5m as an 18-year-old in the 2015 winter transfer window - though Tottenham almost missed out on him, according to former manager and director of football David Pleat.

Having been impressed with Dele's performances at MK Dons, Pleat invited technical director Franco Baldini to watch the teenager in League One action. Spurs stalled on taking action, though, and nearly missed out on his talent, as Pleat highlights what his role at Tottenham has been in recent years.

Tottenham almost missed out on signing Dele

"[My role at Spurs in recent years has been] consultant and scout," Pleat tells FourFourTwo. "I’m very pleased with one or two players who came in where I had an influence, one being Jack Clarke. None of the managers handled him well. He can play.

"There was Dele Alli, too. I took Franco Baldini to watch him and he was on his phone the whole time – he didn’t even watch him. I’ve got six reports on Dele over a period of two years; they should’ve reacted after my first two. Eventually they heard he was going to Aston Villa or Newcastle. They rang me and I said, 'Well, fancy that? Serves you right. You have to get hold of him.' They did the deal really quickly and I persuaded the chairman that £5m wasn’t too much to pay.

"At one stage they could have sold him for over £80m, then things happened. I’m sad because I saw him at 16 and he already had that stature about him, and he could play, too."

While Dele moved to Everton in 2022 in a deal that could have risen to £40m, he is now without a contract, though he continues to train with the Merseysiders as he seeks a return to football.

Pleat, meanwhile, recently stopped working for Tottenham. The 79-year-old isn't intent on retiring now, though, as he also looks to get back into the game in some capacity.

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"I finished at Tottenham recently," Pleat says. "I was the last scout standing – they’ve gone for data completely now. Good luck to them, but there’s a place for scouts. A scout can tell you things data can’t: if the boy is popular with his team-mates, how he reacts when he hasn’t got the ball, what he’s like off the field... Your contacts will tell you that. You’ll know enough people.

"I intend to stay in football, and I’ve been talking to one or two people – I will continue."

Tottenham Hotspur boss Ange Postecoglou has been told to 'keep quiet' after comments he made about promising to deliver success.

The 59-year-old has stated how he 'always wins a trophy in his second season' and the pressure is now on to do so, with Spurs competing on four different fronts this term in the Premier League, FA Cup, Carabao Cup and Europa League.

With their an air of confidence to his recent remarks, some have not taken kindly to his words, especially given it is now a total of 16 years since they last won a major trophy.

Tottenham boss Ange Postecoglou told he should walk the walk, before he talks the talk

"What the hell, Ange. This is going to bite you in the ass," wrote Swedish journalist Tobias Hellgren, in his recent column for footbollskanalen. "I really think it's so cool. You know this when you cockily stick your chin out, promise to achieve something rather difficult to achieve. And so you do it.

"And nothing in Spurs' summer window smacks of a title right away," he continued, with a clear bee in his bonnet. "You smell even less of a title if you sniff the team's season opener. So what the hell? What was that statement good for? All it did was raise the bar, putting unnecessary pressure on himself and his squad in the ultra-competitive environment that prevails in the PL's top tier."

Currently 9th in the Premier League table, the Lilywhites have made an indifferent start to the new campaign, and a response is needed after they threw away a two-goal lead to lose 3-2 against Brighton before the recent international break.

Heung-min Son looks likely to return from injury after choosing not to track back to South Korea for their recent fixtures and boy how could Spurs use his attacking qualities against West Ham United in this weekend's lunchtime kick-off.

"There is a big chance that Postecoglou will have to eat his words at the end of the season as the results look right now," added Hellgren.

"Don't get me wrong: as I said, I love the cocky look. And damn what a ball it would have been if he actually leads the Spurs to a title this season. But first of all, you should probably make sure to put yourself in a position where you have deserved to talk in that way."

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Tottenham have made an impressive start in the Europa League it must be said, winning both of their opening games of the newly renovated group-stage campaign against Qarabag and Ferencvaros respectively.

In FourFourTwo's view, Europe may be the best way for the Lilywhites to lift some silverware this season, especially given they face Manchester City in the last-16 of the Carabao Cup in just a few weeks time. Yikes.

Dele Alli hopes to make a long-awaited return to football after a long spell out - and has his sights set not just on getting back to playing, but re-gaining his place in the England set-up in time for the 2026 World Cup.

The former Tottenham Hotspur midfielder earned his first England gap in October 2015, aged 19, and went on to earn another 35 caps before finding himself out of the frame in 2019.

Dele left Spurs in January 2022, joining Premier League rivals Everton, but he is now a free agent after his deal at Goodison Park expired in the summer.

Dele Alli has eyes set on triumphant return and hopes to regain England place

Dele last played a competitive game while on loan at Besiktas in February 2023, when he suffered a hip injury that required an operation and ruled him out for the rest of the season.

While still recovering from that, the midfielder suffered a groin injury that ultimately also required surgery and ruled him out of the Everton side for the entire 2023/24 season, despite initial hopes that he may be able to return last January.

Dele's remains without a club after his deal at Everton expired, but has been training at Everton's facilities nonetheless to build his fitness back up in hopes of making a return.

The Daily Mail write that Everton are open to the idea of re-signing Dele if he can get there - and that Tottenham Hotspur have generously told the Toffees that he does return to action, they would not hold Everton to a £10m appearance-related agreement made when Everton signed him back in 2022.

That amount was due to be payable upon the England international making 20 appearances for the club, but his tally only reached 13 during his initial spell. Tottenham would reportedly instead be re-paid in performance-related bonus and a sell-on clause.

Dele picked up a slight muscle strain a couple of weeks ago that has set him back slightly, but is not believed to be too serious.

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Dele is limited to playing behind-closed-doors friendlies while he remains unregistered by Everton, but they would be able to sign him as a free agent at any time.

Tottenham Hotspur had just 13 points from their first 14 games of the 1997/98 Premier League season when Gerry Francis was sacked, and chairman Alan Sugar wanted to make a left-field appointment to turn the club's fortunes around.

Seeking the advice of Tottenham's former manager David Pleat, Sugar wanted to learn more about two-time Swiss Super League winner Christian Gross. Pleat, though, knew little of the Swiss manager who had had success with Grasshopper in 1995 and 1996.

Neither did Sir Alex Ferguson, who Sugar believed knew everyone in football. Wanting to figure out if Gross could replace Francis, Sugar enlisted the help of Pleat and Ferguson - not that he took their minimal advice.

Tottenham chairman Alan Sugar appointed Gross with little knowledge

"Sugar asked me if I knew him," Pleat says. "I didn’t, and he said, 'Ring Alex Ferguson – he knows everyone.' He didn’t know much about him, either; I told Sugar, but he went ahead.

"Christian’s agent was Jurgen Klinsmann’s agent, and Klinsmann came back that season. Christian was a nice man but the players didn’t want his tough regime. I told the chairman to give him time but he said, 'You know the mood of the players' and Christian got the sack."

Indeed, after a tough start to the 1998/99 season in which Tottenham lost to Sheffield Wednesday and Wimbledon, Sugar sacked Gross just three games into the new campaign. Pleat briefly stepped in as caretaker, prior to the appointment of George Graham as the permanent boss.

Pleat tells FourFourTwo that he found being the Tottenham director of football "fascinating", however, especially considering Spurs were one of the first clubs in English football to adopt a role for someone to specifically oversee the football operations at the club.

"Alan Sugar was a very clever man: he was the first to want a director of football, because he felt directors didn’t know enough about football and needed someone to help them – a buffer between the manager and the board," Pleat says.

Tottenham Hotspur are said to be lining up a summer attack on Crystal Palace for one of their hottest assets.

Ange Postecoglou's side recruited well after securing a fifth-placed finish in the Premier League last season, bringing in Archie Gray, Dominic Solanke and Wilson Odobert to name a few. Lucas Bergvall and Min-hyeok Yang also arrived, completing a tidy window for the Lilywhites.

But with their plans for further progression on the pitch, Tottenham know more must be done to close the gap on the top four again this season. Aston Villa's example could be followed, with one man tipped to be the difference maker.

Tottenham must buy Ebrechi Eze, says former goalkeeper

Former Spurs goalkeeper Paul Robinson has hailed Crystal Palace star Ebrechi Eze as a potential difference-maker if Tottenham wants to go to the next level. Eze already has three goals and an assist to his name this season, impressing in a relatively weak side managed by Oliver Glasner.

“An attack-minded midfielder is something they are looking at alongside James Maddison,” Robinson told Football Insider. “Eze, depending on how this season goes with Crystal Palace, will sit down and see where his future lies.

“It’ll be a tough one to get done in the winter. He’s under contract until 2027, so come next summer he’ll have two years left on his contract. I fully expect there to be interest in Eze if he has a good season for Palace this year and plays well for England as well.”

Has there been interest from Spurs' camp?

According to Football Transfers, both Arsenal and Tottenham were keen on a move for Eze, but sales elsewhere prevented Palace from agreeing to a deal this summer. The Eagles almost lost Marc Guehi to Newcastle United, but did see Michael Olise join Bayern Munich.

Eze is valued by Palace at £68million and it remains to be seen whether they allow the next talented star from their pool of players to be allowed to leave the club.

Football quiz time – and we're looking for Tottenham's line-up against Wigan in 2009.

It's still Spurs' biggest-ever Premier League win. The Lilywhites thrashed the Latics, thanks to an inspired second half from Jermain Defoe - you can have that one - who notched five.

It's still a joint record for most goals in a top-flight fixture since 1992. So who else played?

We've arranged the XI out for this Premier League quiz and we're only looking for surnames only. We can tell you that Harry Redknapp was the manager, too. No more hints from us!

But… you can have some from Kwizly. Simply sign in and you can get a hint on this Tottenham quiz by clicking the Hint button to get the next letter of the next player you're currently trying to guess.

Remember to tweet your scores @FourFourTwo and share with your mates…

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While Tottenham Hotspur goalkeeper Guglielmo Vicario had a torrid Sunday afternoon conceding three times to Brighton at the Amex Stadium, one of Spurs' former 'keepers enjoyed saving three penalties during one game.

Vicario could do little as Tottenham blew a 2-0 lead to Brighton, but the footballing drama clearly wasn't reserved for just the Premier League at the weekend.

Indeed, as during Girona's 2-1 win against Athletic Bilbao 2-1 in La Liga on Sunday, one former Tottenham Hotspur player put in a heroic performance to ensure all three points stayed in Catalonia.

Ex-Tottenham Hotspur goalkeeper Paulo Gazzaniga pulls off heroics

Penalties were clearly the narrative referee Juan Luis Pulido Santana wanted to stick to at Girona's Estadi Montilivi, as he awarded three during the match. The first came in the 28th minute, when a VAR review saw Athletic Bilbao earn their first spot-kick of the afternoon.

Striker Alejandro Berenguer Remiro stepped up, but Gazzaniga saved to keep the scores level. Girona's Yasser Asprilla then opened the scoring for the Catalan side later in the first half, before Oihan Sancet levelled just minutes later.

Then, early in the second half, Athletic Bilbao were awarded another penalty. This time Inaki Williams stepped up, with Gazzaniga saving once more. However, the former Tottenham man had stepped off his line in doing so, leading to the penalty being retaken.

The Argentine atoned for his error, stopping Ander Herrera's spot-kick to make it three penalty saves in the game. It proved crucial, too, as Cristhian Stuani scored the winner for Girona in the 99th minute - from a penalty of his own - after Aitor Paredes had been sent off for Athletic Bilbao.

Gazzaniga faced 13 shots in total during the game, though only four were on target - including two of the penalties he saved (Williams' penalty doesn't count towards the stats due to it being retaken).

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During his four years at Spurs, Gazzaniga made 37 appearances in all competitions. He was signed from Southampton where he had played for six years, before a loan move to Elche then saw him drop into the Championship with Fulham in 2021/22.

Another loan came in 2022/23, this time to Girona, followed, before he joined permanently at the beginning of the 2023/24 campaign. The 32-year-old has since become the No.1 at Girona, helping the Spanish side into the Champions League.

Tottenham Hotspur missed out on signing Robin van Persie while he was just a teenager, with former director of football David Pleat unimpressed by how the Dutchman looked when coming on during a game for Feyenoord.

Van Persie ultimately ended up moving to Arsenal, with that decision having stuck in the mind of Pleat.

Pleat spent 26 years as a manager, taking charge of the likes of Luton Town, Leicester City, Sheffield Wednesday and Tottenham Hotspur. Towards the end of his career, Pleat moved upstairs to become the Spurs director of football - with two stints as caretaker boss and one season in the dugout at White Hart Lane, too.

How Tottenham missed out on signing Robin van Persie

During his time, Pleat missed out on a couple of high-profile signings, though failing to recognise the talent of Robin van Persie still sticks in his mind. When asked who he regrets not signing during his career in football, Pleat highlights a few high-profile stars alongside Van Persie.

"At Tottenham, John Barnes’ agent told me he was leaving Watford: £750,000," Pleat exclusively tells FourFourTwo. "But I had Waddle and Hoddle. I didn’t take Barnes and he went to Liverpool.

"At Luton we had Stuart Pearce training for a week with the reserves when he was at Wealdstone; I asked the coach what he was like and he said, 'OK.' I should’ve played him in an 11 vs 11 and made everyone play properly: then we would have seen his character.

"Then as a director of football, at Tottenham, I went to Feyenoord to see Robin van Persie. He came on as a sub, shirt out of his shorts, socks rolled down, looking a right mess. Steve Rowley at Arsenal had decided not to sign him, but they went for a second look and decided to take a chance."

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Indeed, in the summer of 2004 Arsenal signed Van Persie for £2.75m, converting him from a left winger into a centre-forward. That proved a masterstroke from Arsene Wenger, with Van Persie going on to score 132 goals in 278 games for the Gunners prior to his move to Manchester United in 2012.

In total, Van Persie ended up scoring 148 Premier League goals during his 11 years in England, winning the Premier League and FA Cup in that time, too. For Pleat, failing to take a second look at the young Dutchman for Feyenoord was clearly a mistake.

Tottenham Hotspur were left reeling when Sol Campbell decided to leave the club and join bitter rivals Arsenal on a free transfer in the summer of 2001, but Spurs' then director of football David Pleat reveals there was nothing they could do to stop the move from happening.

For Arsenal fans, it's perhaps the greatest Premier League transfer ever - in FourFourTwo's opinion, it's the second-most controversial move in football history, behind only Luis Figo's switch from Barcelona to Real Madrid.

Tottenham's club captain at the time, Campbell became the first player since Pat Jennings to move from White Hart Lane to Highbury. Crucially, he did so as part of a free transfer, meaning the club he had spent more than a decade at were gaining nothing from the deal whatsoever.

Tottenham tried everything they could to keep Sol Campbell

For Campbell, trophies were the ultimate objective, and he didn't feel Tottenham could help him deliver that ambition, while Arsenal ultimately would.

David Pleat was the director of football at Tottenham at the time, offering Campbell a contract which would have made him the club's highest-ever paid player. That didn't prove enough, however. Pleat and Tottenham's manager George Graham were simply unable to convince the centre-back to stay.

"We did everything we could, but there was no chance – what he was going to get at Arsenal was way out of our range," Pleat exclusively reveals to FourFourTwo. "To be fair to Sol, I’d met him previously with [Alan] Sugar, and Sol believed we weren’t spending enough to get better players in. I told him that it isn’t always possible and you have to be patient.

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"I found him a decent guy. But he decided that he needed to move for his own career.

"Later, Sugar said, 'You and George Graham were so stupid: you should have kept him out of the team and he would have signed because he would’ve lost his England place.' Myself and George had decided that we weren’t going to leave him out and cut our nose off to spite our face. He was the best centre-half we had."

For much of the last decade Tottenham Hotspur were driven by boyhood Arsenal fan Harry Kane – at least until their star man departed for Bayern Munich last summer.

But Kane may have never had the opportunity to breakthrough back in 2014, had Tottenham signed legendary Peru striker Paulo Guerrero. In January 2013, Guerrero was looking to looking to leave Brazilian side Corinthians and return to Europe having previously spent 12 years in the Bundesliga.

The Premier League, and specifically Tottenham Hotspur, were his first choice. However, it was ironically a former Arsenal player who ended up scuppering the deal and denying Guerrero the chance to move to North London.

How Arsenal's Edu blocked Tottenham from signing Paulo Guerrero

Former Arsenal midfielder – part of the immortal ‘Invincibles’ team - and current Gunners sporting director Edu was responsible for Guerrero’s transfer falling through.

The Peru legend has revealed that while at Corinthians, Spurs were close to signing him in January 2013. That was before a last minute intervention, where Edu - then Corinthians director of football - promised Guerrero a pay rise to stay.

Speaking to the D&T programme, Guerrero said: “When I arrived at Corinthians, I said to myself: ‘I win the Club World Cup and I’ll go back’.

“Did I have opportunities to return to Europe? Many, but Corinthians didn’t want to sell me or didn’t want to negotiate. The last offer came from Tottenham, which was a loan-purchase option.”

“I went with the proposal to talk to Edu, who is now Arsenal’s director, and I said ‘I have this, please’. His response was: ‘Do you want the crooked thing to kill me, Paolo? Rest assured that here you will be the highest paid footballer in South America’.

“He didn’t comply. I didn’t renew with Corinthians because the proposal they made me wasn’t within what I think I deserved. I believed that because I was Peruvian, they were not valuing me.”

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Guerrero eventually did leave Corinthians, but not until 2015, where he instead joined Brazilian rivals Flamengo rather than move to England.

Now 40, Guerrero has still yet to return to Europe since leaving Hamburg in 2012, but remains a legend in South America, winning 122 caps for his country.

After failing to land Guerrero, later that year Spurs instead signed Spanish forward Roberto Soldado. However, Soldado struggled to adapt to English football, paving the way for Kane’s opportunity to break into the first team in 2014.