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Tottenham's 10 best victories against Man Utd

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Tottenham Hotspur welcome Manchester United to north London on Sunday for a Premier League clash that, in the not-so-distant past, would have been a top-of-the-table encounter.

However, this season, it's a bottom-half affair. Instead of vying for European football, both sides will be battling to distance themselves from the relegation zone.

With United in 13th on 29 points from 24 games and Spurs in 14th with 27, it's safe to say it's been a poor season for both teams.

For the Red Devils, off-field upheaval, poor recruitment and a lack of quality on the pitch seem to be the culprits. Meanwhile, Spurs have had their own struggles, with injuries playing a significant role in their poor campaign as manager Ange Postecoglou has been constantly losing key players like Micky van de Ven, Cristian Romero and Dominic Solanke week after week.

Postecoglou’s job is certainly under pressure, but a win over United could ease that tension, even if just for a week or two.

He'll be hoping his side can replicate some of their best-ever results over United, 10 of which we've recounted here.

Tottenham mostly had a forgettable season in 1995/96, finishing 8th in the Premier League, and crashing out of the League Cup and FA Cup in the third and fifth rounds respectively.

Perhaps the highlight, however, was their 4-1 thumping of would-be champions Manchester United at White Hart Lane on New Year's Day in 1996.

Teddy Sheringham, who would later join United in 1997, opened the scoring on the day, while Sol Campbell and Chris Armstrong, who scored a brace, were also on the scoresheet.

Manchester United had already been crowned Premier League champions when they travelled to White Hart Lane in May 2001.

Clearly having taken their foot off the gas after defeats to Derby County and Southampton, they slumped to another loss against Spurs, who were more than happy to take advantage of their complacency.

While not a classic in the traditional sense given that nothing was really on the line, Willem Korsten's opening goal - chesting the ball down on the edge of the box before volleying it over United goalkeeper Raimond van der Gouw - was arguably one of the best Spurs have ever scored against the Red Devils.

Tottenham started the 2018/19 Premier League season in fine form, winning their first three games, the last of which was a commanding 3-0 victory over Manchester United.

After a goalless first half, Harry Kane broke the deadlock in the 50th minute, before a brace from Lucas Moura sealed the win for Mauricio Pochettino's side.

However, Spurs' bright start came to an abrupt halt a week later when they suffered a 2-1 defeat to Watford at Vicarage Road.

En route to winning the League Cup in 1998/99, Tottenham had to overcome Manchester United in the quarter-finals. United, sitting 2nd in the Premier League, were heavy favourites against Spurs, who were struggling in 12th place at the time.

However, a brace from Chris Armstrong and a stunning long-range strike from David Ginola, who tormented United’s defence that night, secured a memorable 3-1 victory.

With United securing a treble, Spurs were the only side to stop the Red Devils in this particular season with this win.

In a modern-day Spurs-United clash in December 2024, Ange Postecoglou’s side triumphed 4-3 over Ruben Amorim's Manchester United in the League Cup quarter-finals.

Spurs raced into a three-goal lead with a Dominic Solanke brace and a goal from Dejan Kulusevski, before United fought back through goals from Joshua Zirkzee and Amad Diallo after some calamitous defending.

Son Heung-min made it 4-2 late on, but veteran United defender Jonny Evans headed home in injury time to set up a nervy finish. Spurs held on to secure the win, setting up a semi-final clash with Liverpool, where they were beaten 4-1 on aggregate.

Back in the late 1980s, Tottenham were the superior side to Manchester United, who were still finding their feet under Sir Alex Ferguson.

The Lilywhites made their superiority clear when the two teams met in the First Division in May 1987, running out as comprehensive 4-0 winners thanks to a brace from Mitchell Thomas and goals from cousins Paul and Clive Allen.

Spurs finished the season in third, while United ended up in 11th.

Tottenham won the FA Cup in 1960/61 and looked poised to repeat the feat the following year when they faced Manchester United in the semi-finals.

In front of 65,000 fans at Hillsborough, the Lilywhites put on a stunning display, thumping the Red Devils 3-1, with Jimmy Greaves, Cliff Jones and Terry Medwin all finding the net for Bill Nicholson’s side.

Spurs went on to defeat Burnley by the same scoreline in the final, securing back-to-back FA Cup triumphs.

When Tottenham travelled to Old Trafford in September 2012, the Lilywhites hadn’t beaten Manchester United in any competition in over a decade, with their last win coming back in May 2001.

However, an early goal from defender Jan Vertonghen set the tone for change, before a second from Gareth Bale seemed to seal it.

After the break, there were three goals in three minutes. United pulled one back through Nani and Clint Dempsey extended Spurs' lead before Shinji Kagawa made it 3-2.

United pushed for an equaliser, but Andre Villas-Boas' side held firm.

Tottenham bid farewell to White Hart Lane in style, capping their most successful Premier League season to date with a 2-1 victory over Man Utd in the famous ground's final game.

Victor Wanyama scored early on before Harry Kane's finish just after the restart put Mauricio Pochettino's side in cruise control. Wayne Rooney would score the final goal at the old stadium but that did little to dampen the home team's spirits as they celebrated finishing second in the table - above Manchester City and Arsenal.

Spurs moved to Wembley the season after, though they are yet to top their 86-point haul from 2016/17, where they remained unbeaten at home and finished above rivals Arsenal for the first time in over 20 years.

In one of the most iconic Tottenham displays of recent times - and certainly their best against United - Spurs dismantled Ole Gunnar Solskjaer's side at Old Trafford in October 2020, hammering United 6-1.

United took the lead with an early Bruno Fernandes penalty, but from that moment on, it was all Tottenham.

Tanguy Ndombele started the rout, before two goals apiece from Harry Kane and Son Heung-min, plus a rare strike from defender Serge Aurier, sealed a momentous victory for the Lilywhites.

Tottenham hold direct talks with £55m star as Bayern give up on keeping him

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Tottenham Hotspur have reportedly held direct talks with another Bayern Munich star recently - following their January loan deal for his Bavarian teammate Mathys Tel - and it is believed Vincent Kompany's side are resigned to losing him this summer.

Mathys Tel impresses for Tottenham after Bayern Munich switch

In what was one of the most dramatic winter window transfer stories, Tel pulled a full U-turn on his decision to join Spurs after originally snubbing the club's advances.

Chairman Daniel Levy personally flew to Munich for sit-down talks with the 19-year-old, who initially rejected the Lilywhites and their board member's offer to join Spurs before deadline day (Florian Plettenberg).

However, while Levy flew home empty-handed, it was under-fire Tottenham boss Ange Postecoglou who apparently played a major role in helping to convince the teenager to make a move to north London.

"Daniel Levy flew to Munich last week because Johan Lange feared that his meeting and presentation with Mathys Tel didn’t have the desired impact," said L'Equipe reporter Loic Tanzi.

"After meeting with Levy, Tel communicated that he wasn’t going to join Spurs. It was as much about showing that he wouldn’t be forced into something by Bayern as it was about not being convinced by Spurs. Sunday evening, Ange Postecoglou spoke with Tel over the phone. Postecoglou put forward how he planed to use Tel, expressed how much he valued Tel’s versatility and speed, and expressed that he thought Tel could torment Premier League defences with his qualities."

Tel pen to paper on a temporary N17 switch, which includes an option to buy for in and around £50 million, and he's since impressed on-lookers with his enthusiasm in an otherwise dismally out-of-form side.

The Frenchman bagged his first goal for Tottenham in a 2-1 defeat to Aston Villa in the FA Cup, and according to CaughtOffside, Tel could be joined at Hotspur Way by his Bayern colleague Leroy Sané.

Tottenham hold direct talks with Leroy Sané as Bayern stance revealed

The German, who cost Kompany's side around £55 million to sign from Man City in 2020, is set to be a free agent at the end of this season.

Bayern, despite their best efforts to tie him down with fresh terms, have "all but given up" on trying to keep the 29-year-old - giving Spurs a golden opportunity to snap him up at zero cost.

CO write that Tottenham have held recent talks with Sane, and could hold a financial advantage over Barcelona in the race for his signature. The Lilywhites have apparently emerged as "serious contenders" for his signature, which bodes well for next term considering Sane's obvious quality.

Cost £25m, now worth 132% more: Spurs hit the jackpot on "world-class" ace

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It's been a brutal season for Tottenham Hotspur that only seems to get more so by the week.

Ange Postecoglou's side have been utterly ravaged by a seemingly endless string of injuries to key players all over the pitch, and it has understandably affected their campaign.

In the Premier League, the North Londoners have lost more games than they've won, and over the last seven days, they have been knocked out of the FA Cup and League Cup.

With all that said, there are at least a few players who can come out of this horror season with their heads held high, including one who is worth millions more than he was when Spurs signed him.

The Spurs stars who can hold their heads high

Now, while the aforementioned injuries haven't helped in the slightest, the team has been underwhelming at best this season, although a few players have stood out for the right reasons, such as Dominic Solanke.

The £65m man is the club's record signing, and while he did get off to a somewhat slow start, he eventually found his feet and showed the fans that his fee was entirely justified.

For example, prior to his injury, the former Bournemouth star scored 11 goals and provided six assists in 29 appearances, which comes out to an average of a goal involvement every 1.70 games.

From the frontline to the back, someone who has been a surprise hit this year has been Djed Spence.

We say surprise as it looked like he was on his way out of the club in the summer and wasn't even included in the first Europa League squad.

However, as the defence started falling like flies, Postecoglou was forced to call upon the Englishman, and it was a good thing he did, as the 22-year-old is now arguably their best full-back.

He might not quite be able to whip a ball as well as Pedro Porro, but he's no slouch going forward, and unlike some of his teammates, he's imposing when it comes to the defensive side of the game.

With that said, neither he nor Solanke has been Spurs' best player this season; that title goes to someone else, someone whose valuation has exploded since joining the North Londoners.

The Spurs star whose valuation has exploded

Despite their position in the table, there are several incredibly valuable players in the Spurs squad, like Solanke, Cristian Romero and Micky van de Ven.

In this instance, though, the player in question is none other than Dejan Kulusevski, who made his move to N17 permanent in 2023 for a fee said to be in the region of £25m.

However, he's worth a lot more than that today, with the CIES Football Observatory valuing him at around €70m, which converts to about £58m, representing a 132% increase on the fee paid by the Lilywhites.

Now, that is undoubtedly a lot of money, and it's probably fair to say the last few weeks have not seen him at his very best, but when we take a look at the season as a whole, it's clear that he's been the club's best player and more than deserves such a valuation.

For example, in just 39 appearances, which have seen him play in midfield and out wide, the "world-class" international, as dubbed by talent scout Jacek Kulig, has scored nine goals and provided ten assists.

That means the 24-year-old game-changer is averaging a goal involvement every 2.05 for a team struggling in the bottom half of the Premier League table - talk about impressive.

Ultimately, this season has been nothing short of a disaster for Tottenham, but even in such a campaign, players like Spence, Solanke and even Kulusevski have shown that they have what it takes to be a part of the next great Spurs side.

He's outscoring Solanke: Spurs almost signed unreal PL Golden Boot winner

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After finishing in fifth place last season, there was a hope from fans that Tottenham Hotspur would be able to go kick on this year, a hope that remains very much unrealised.

Instead of fighting for a Champions League place, Ange Postecoglou's side sit in the bottom half of the Premier League table with more losses than wins, and a big reason for that is their incredible bad luck with injuries.

The North Londoners have missed practically their entire backline for much of the campaign and are now without top scorer Brennan Johnson and record-signing Dominic Solanke.

The English forward has been brilliant for the Lilywhites this season, but interestingly, he's being outscored by another former Premier League superstar who almost signed for Tottenham over ten years ago.

Spurs' best attackers in 2024/25

While defence has undoubtedly been a major problem for Spurs this season, largely thanks to injuries, the team have still been a relatively potent attacking force for much of the campaign, as demonstrated by their 48 league goals, a tally only bettered by Arsenal and Liverpool.

The most prolific player for Ange this year has been Johnson, who, after a slow start to the campaign that saw him deactivate his Instagram account due to fan abuse, has racked up a stellar haul of 12 goals and three assists in 32 appearances, only 22 of which have been starts.

Close behind the Welshman is the club's £65m man, Solanke, who, in his first campaign for the North Londoners, has already scored 11 goals and provided six assists in just 33 appearances, which comes out to an average of a goal involvement every 1.94 games.

The only other player in the squad to have reached double figures for goals this term is Son Heung-min, who has found the back of the net on ten occasions and provided eight assists, for good measure, all in just 33 games.

The top five is rounded out by Dejan Kulusevski, who has produced 19 goal involvements in 39 games, and James Maddison, who has managed to rack up nine goals and six assists in his 31 appearances thus far, of which only 21 have been starts.

In all, despite their lacklustre form this season, Spurs do have several incredibly talented attackers to choose from when all fit. However, for all his hard work, Solanke is being outscored by a former Premier League star who almost signed for the club in the past.

The free-scoring forward Spurs almost signed

As with practically every major club, there are always countless examples of players they could have signed in the past who go on to great things down the line.

However, in this instance, Spurs had to watch Pierre-Emerick Aubameyang take the Premier League by storm and win an FA Cup with Arsenal years after they passed up on the chance to bring him to the white side of North London.

The "tremendous" Gabonese international, as dubbed by Arsene Wenger, was shown around the club in 2012 but was never contacted afterwards.

According to former Spurs player Ronny Rosenthal, who was working with the striker at the time, then-manager André Villas-Boas made the decision not to pursue him.

In the decade and a bit since, the Laval-born superstar has gone on to score 141 goals in 213 games for Dortmund, 92 goals in 163 games for the Gunners, where he picked up a Premier League Golden Boot and FA Cup, 13 goals in 24 games for Barcelona, three goals in 21 games for Chelsea, 30 goals in 51 games for Marseille and now 12 goals in 20 games for AL-Qadsiah in Saudi Arabia.

That means the "unreal" goal machine, as dubbed by journalist Jonas Adnan Giæver, is currently outscoring Solanke at the ripe old age of 35, and while it is undoubtedly a lower standard than in England, you only need to look at his sensational tally in France last season to see that he could still get the job done in a top five league.

Ultimately, Spurs won't be losing any sleep over not signing Aubameyang back in 2012, especially not when a certain Harry Kane would soon emerge.

That said, it's interesting to imagine what it would have been like to see him in the white half of North London and not the red.

Tottenham targeting £83m star as they begin work to replace Cristian Romero

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Tottenham Hotspur are said to have identified a potential replacement for Cristian Romero in a marquee centre-back, as they begin working on potential successors for the Argentine in the event he departs this summer.

Cristian Romero linked with high-profile move to Real Madrid

Carlo Ancelotti and Real Madrid are widely reported to be in the market for another defender this summer, so much so that they've allegedly earmarked Romero as a top centre-back target as they look to the Premier League for options.

The Galacticos have been left short of defensive options on more than one occasion due to injuries this campaign, prompting the La Liga giants to consider bolstering their backline ahead of 2025/2026.

Romero is on Real's shortlist of potential centre-back signings, alongside Arsenal star William Saliba, but chairman Daniel Levy won't be letting him go on the cheap.

Indeed, it is believed by some media sources that Spurs have slapped a mammoth £150 million price tag on Romero, while other reports suggest Tottenham are ready to make the World Cup winner their highest-paid player to fend off Madrid's interest.

The former Atalanta star has been a very sore miss for under-fire boss Ange Postecoglou, who's suffered without both Romero and Micky van de Ven to reinforce their high line, and his injury is taking more time to heal than previously expected.

"Romero is a bit of a tricky one. We are not really sure yet. There is still some work he needs to do," said Postecoglou on Romero recently.

"It’s just a slower healer with him, and it is one we are looking at on a week-to-week basis. Again, he has been out for quite a while. As with all the other long-term ones, we are just taking our time."

Tottenham eye Antonio Silva as potential Cristian Romero replacement

While Spurs are not eager to sell the 26-year-old any time soon, they're making contingency plans in the event they're forced to do a deal with Real or any other interested club.

According to journalist Graeme Bailey, writing for The Boot Room, Tottenham are working on replacements for Romero, and have identified marquee Benfica defender Antonio Silva as a target.

The Portugal international's contract includes an £83 million release clause, but there is always the possibility that the Lilywhites can negotiate a fee far lower than this valuation.

Silva, still just 21-years-old and an impressive performer in the Primeira Liga, could be worth the effort - especially going by Jan Vertonghen's verdict on the player.

How Levy is preparing to stop £150m Tottenham star from joining Real Madrid

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A report has shared how Tottenham Hotspur and chairman Daniel Levy are preparing to stop a big-name star in their squad from joining Real Madrid, with a seismic offer said to be at the ready.

Postecoglou slammed after Tottenham defeat to Aston Villa

It isn't exactly the happiest time to be a Spurs supporter right now, with under-fire manager Ange Postecoglou bearing the brunt of fierce criticism amid a lacklustre 2024/2025 campaign.

The Lilywhites crashed out of both domestic cups recently after defeats to Liverpool and Aston Villa, and calls for Postecoglou's dismissal have seriously heightened since their 2-1 defeat at Villa Park in the FA Cup on Sunday.

It would be unfair on the Australian to not bring up Tottenham's extensive injury list, which includes absolutely pivotal first-team players who haven't been available for months, but critics have made a case of suggesting that recent results still haven't been good enough.

"It's time to go now, Ange is out of his depth," said pundit Jamie O'Hara in the aftermath of Spurs' 2-1 loss at Villa.

"[Unai] Emery is on a different planet compared to him and his players bopped us off the park. Should have been five, we're like a reserve team playing in academy games that don't matter, it's crazy."

O'Hara's talkSPORT colleague, Gabriel Agbonlahor, also went one further by calling Tottenham the "laughing stock" of the Premier League.

"You've become the laughing stock of the Premier League, especially when Ange Postecoglou said those words, 'I always win something in my second season,'" Agbonlahor said.

"You just knew the pressure was on. Tonight, Villa had 16 shots, Jacob Ramsey could have taken two match balls home. The chances we missed... it was easy. Where are the tactics?"

If results continue in this manner, especially after his key stars return from injury, questions will have to be asked in regard to Postecoglou's future.

Tottenham have reportedly done their due-diligence on potential replacements for Postecoglou, with the likes of ex-Borussia Dortmund boss Edin Terzić, Bournemouth's Andoni Iraola and Brentford's Thomas Frank all linked this week.

According to some reports in Italy, even close advisor Fabio Paratici is urging Spurs to consider Simone Inzaghi, who guided Inter Milan to the Serie A title last season.

How Levy is preparing to stop Romero from joining Real Madrid

According to The Boot Room and journalist Graeme Bailey, elite clubs are also looking to poach some of Tottenham's most crucial players amidst this crisis.

Real Madrid are believed to have identified defender Cristian Romero as one of their top centre-back targets for the summer window, despite Spurs placing a mammoth £150 million price tag on his head.

This could come as a worry for Spurs, but according to Bailey, Tottenham are ready to make Romero their highest-paid player with a lucrative contract offer to fend off Carlo Ancelotti's side.

The Argentine World Cup winner is among Postecoglou's star absentees of recent months, and his absence has been sorely felt on the pitch. Spurs need to ensure his long-term future is secured, with or without their current manager at the helm for next term.

Tottenham manager target ready to leave club with Postecoglou sack "closer"

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Tottenham Hotspur have drawn up a list of alternative managerial options to Ange Postecoglou, with the Australian under mounting pressure at N17 amid a very disappointing second Premier League campaign in charge.

Tottenham crash out of domestic cups as critics call for Postecoglou sacking

In the space of a few days, Spurs crashed out of both the Carabao Cup and FA Cup respectively, after being hammered by Liverpool at Anfield and falling short away to Aston Villa.

Postecoglou's extensive absentee list has been a point of serious debate, with a plethora of key first-team players consistently unavailable since mid-November, in what is considered one of the worst injury crises we've witnessed in recent campaigns.

Guglielmo Vicario, Micky van de Ven and Cristian Romero - the backbone of Spurs' team - have been out for long periods alongside a host of other pivotal players. This has undoubtedly crippled the Lilywhites, but critics make a stern case that results simply need to be better regardless.

Postecoglou now faces a mammoth test at home to Man United, and another crucial 90 minutes when it comes to determining his long-term suitability for the Spurs dugout.

"The pressure will only get more intense, and I think that’s when he’ll be sacked, if players come back from injuries and there isn’t an immediate turnaround in form. That’s what they’re expecting and hoping for – players to come back and results to improve," said former Tottenham scout Mick Brown this week (Football Insider).

“If it doesn’t happen, the blame will be placed on the manager. They’ve put so much emphasis on these injured players, so they’re willing to stick with him until he gets them back into the team.

“But if they come back and things don’t go well, it doesn’t bode well for Postecoglou’s position.”

Thomas Frank ready to leave Brentford as Tottenham target him

According to TEAMtalk, Postecoglou's potential sacking is edging "closer" after their torrid cup results, and Brentford manager Thomas Frank is one of the options they're considering as his potential replacement - should they decide to pull the plug.

Previous reports indicate that Frank is one of Spurs' top managerial targets if Postecoglou leaves, and this is echoed again by TEAMtalk, who also share the Dane's stance on leaving his current club this year.

The outlet reports that Frank is ready to leave Brentford for his next challenge at the end of the season, so if chairman Daniel Levy opts not to continue with Spurs' current head coach, they could have an opportunity to tempt the former with a move to north London.

The 51-year-old, who's done an impressive job at Brentford on a shoe-string budget, is highly regarded by those within Spurs - and he's apparently an option they looked at to replace Antonio Conte before they decided to hire Postecoglou.

Tel will love him: Levy looking at "incredible" Ange upgrade for Spurs

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Football is a brutal business, and while he still has his supporters, Ange Postecoglou's time as Tottenham Hotspur manager could be coming to an end.

The Australian has transformed the Lilywhites from a dismally dull team into one of the most entertaining ones to watch in English football.

However, his ultra-attacking brand of football and horrendous luck with injuries has seen his side fall to 14th place in the Premier League and be knocked out of both domestic cup competitions this season.

While he might be able to steady the ship when his players start to return, he may not have the chance, as recent reports have suggested that he might be just a game away from the sack, which could see the club bring in a manager who'd be perfect for Mathys Tel and the other youngsters in the squad.

Tottenham's manager search

According to a recent report from TEAMtalk, the Tottenham board are set to decide on Postecoglou's future following the game against Manchester United on the weekend, which looks like it could be a tough test for the weary Lilywhites side.

In worse news for the Australian, the report has revealed that the club has recently identified two potential replacements already plying their trade in the Premier League: Brentford boss Thomas Frank and Bournemouth's Adoni Iraola.

However, it seems incredibly unlikely that either of them will leave their current sides mid-way through the campaign, which could mean Daniel Levy and Co turn their attention to a European manager who's currently out of a job and was quite heavily linked with Spurs last month: Edin Terzić.

The former Borussia Dortmund boss has been out of work since leaving the German behemoths in June last year, and while appointing him as the new Spurs boss could raise a few eyebrows, there are some reasons why it could be a brilliant idea.

Why appointing Terzić would be a great idea

There are two main reasons why Terzić could be the perfect manager to replace Postecoglou at Spurs, and the first is how he develops young stars.

It would be fair to say one of the few positives to come out of this season for Spurs is the emergence of Mikey Moore from the academy and how well Archie Gray, Lucas Bergval, and now even Tel have adapted to the first-team.

Therefore, it would make sense to bring in a head coach with a proven track record of developing talent, and thanks to his time with Dortmund, the German certainly has that.

For example, while the talent has always been there, he was able to platform Jude Bellingham in a way that took him from a prospect to a Galactico in the space of a few years.

He helped Erling Haaland continue his development as well, and in an interview with the Bundesliga website, the Norwegian superstar was more than happy to praise his then-manager, saying, "Edin and I have a good relationship ever since I came here and we've been talking a lot about different things."

So, if he has been able to help incredible prospects reach world-class status in the past, why wouldn't he be able to do the same with someone like Tel, who produced 16 goal involvements in just 1406 minutes of first-team football last season?

The second reason hiring the "incredible" 42-year-old, as dubbed by former Dortmund CEO Hans-Joachim Watzke, would be a good idea is that he led Dortmund to German Cup glory in 2021, came painfully close to winning the league and Champions League, and has a better record in his last stint with the team than Postecoglou has with Spurs.

For example, in 96 games, he oversaw 55 wins, 20 draws, 21 defeats and an average of 1.93 points per game, while the Australian has taken charge of 80 games since getting the job in 2023 and overseen 39 wins, 11 draws, 30 losses and an average of just 1.60 points per game.

Ultimately, if Spurs are going to get rid of Ange in the middle of the season, then signing Terzic might be their best option, not only because he did well with Dortmund but also because he has a proven track record of getting the most out of young talents, which could be perfect for the likes of Moore, Gray and Tel.

Signed by Conte, now worth 266% more: Spurs hit the jackpot on amazing star

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Tottenham Hotspur have been through so many seismic changes over the last few seasons that it feels like an age ago that Antonio Conte was in the hot seat.

Bringing the Italian manager to N17 in 2021 was an ambitious move from Daniel Levy and Co, as while he had a reputation as being rather hard to work with, he was a proven winner and had done so across town with Chelsea.

However, as has been the case so many times before, the former Inter Milan boss eventually left the Lilywhites in a cloud of smoke with nothing much to show for his time.

That said, while he did make some mistakes in N17, Conte did at least make some good signings, including one player whose valuation has soared since his arrival.

Conte's best Spurs signings

Before we get to the player in question, it's worth looking at a couple of Conte's best signings from his time with Spurs, starting with one who might just be the team's best player: Dejan Kulusevski.

The Swedish international initially joined the Lilywhites on an 18-month loan deal in January 2022, and while he's not always been the most consistent player, he's shone at times this season.

For example, in just 39 appearances, which have seen him play in midfield and out wide, the Stockholm-born maestro has scored nine goals and provided ten assists, which comes out to an impressive average of a goal involvement every 2.05 games.

Moving into defence, one of Conte's most interesting signings was Djed Spence, who joined the club from Middlesbrough for £20m in July 2022, and it would be fair to say his journey to becoming a first-team regular has not been a simple one.

He spent the second half of the 22/23 campaign on loan with Stade Rennais; then he moved to Leeds United for the first half of the 23/24 campaign and Serie A side Genoa for the latter half.

It looked as if he was going to be sold last summer, and he wasn't even included in the club's Europa League squad, but the team's incredible injury crisis this season saw him finally get some game time, and since then, he has looked like one of the best players in the squad.

He can play on either side of the back four, has the attacking ability to get forward, and has the defensive solidity that makes him a tough challenge for opposition attackers, but he's still not the player in question.

The Conte signing whose valuation has exploded

Interestingly, the signing in question is someone who could either form a brilliant partnership with Spence when he returns from his injury or even rival him for a place at left-back.

Destiny Udogie joined Tottenham in the summer of 2022 from Serie A side Udinese for around £15m plus add-ons but stayed with the Italian outfit for a season-long loan, so when he finally made his debut for the club the following year, it was under Postecoglou and not Conte.

The Verona-born full-back was a relative unknown at the start of last season, but by the end, he was considered one of the most exciting young left-backs in the Premier League.

So much so that he was the first Spurs player to be nominated for the Premier League's Young Player of the Season award.

In all, the "monster" talent, as described by journalist Travis Levison, has made 53 appearances for the North Londoners, in which he's scored two goals and provided four assists, and while he has not necessarily hit the heights of last season this year, he's still an incredibly promising player.

Football Transfers certainly seem to agree, as they have valued the Italian at up to a whopping €66m, which converts to about £55m, which is a staggering 266% increase on the fee the club paid for him just over two years ago.

Ultimately, while Conte left Spurs with little to show for it in terms of medals, he did at least bring in several talented players who could be a part of the next great Tottenham side.

Tottenham open to axing £190k-a-week star in previously "unthinkable" sale

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Tottenham Hotspur chiefs are now believed to be weighing up the possibility of selling a key player in their squad, with under-pressure head coach Ange Postecoglou and co eyeing a potential summer revamp.

Postecoglou pressure grows as Tottenham crash out of FA Cup

Spurs crashed out of the FA Cup fourth round after a 2-1 defeat to Aston Villa in the Midlands last weekend, meaning the Europa League is their only chance of winning any silverware this season.

The Lilywhites' solid summer transfer window, where they completed a £65 million deal for England striker Dominic Solanke, and their very promising 2023/2024 campaign under Postecoglou allowed supporters to go into this season with cautious optimism.

However, a torrid run of results, partly due to the thread-bare squad's serious injury problems, have left Spurs 14th in the Premier League table with four defeats from their last five games.

Their latest hammer blow courtesy of Villa has prompted even more calls for Postecoglou to receive the axe from chairman Daniel Levy, even if the Australian is missing over 10 senior first-team players right now.

"One by one the safety nets protecting Ange Postecoglou from a catastrophic fall into footballing oblivion are falling away," said journalist Ian Ladyman of The Daily Mail (via football.london).

"If Liverpool hacked at a cord in demolishing Postecoglou’s Tottenham in one domestic cup competition last Thursday, then Aston Villa methodically undid a knot or two in the other one at Villa Park.

"Now there is almost nothing left but a long drop down to the darkness for the Tottenham manager. Spurs remain in the Europa League, but that’s where the good news begins and ends. The Premier League became an embarrassing and soulless slog long ago. Tottenham, weighed down by diminished confidence and a long injury list, sit in 14th position.

"Tottenham have gone from a ‘must watch’ team to a ‘can’t bear to watch’ team, and it’s now up to chairman Daniel Levy in terms of what he wishes to do about it."

Tottenham considering Son Heung-min sale this summer

Postecoglou also hasn't been helped by a lot of his big-name players, with £190,000-per-week club captain Son Heung-min under-performing in recent months.

Son was praised for his stellar form at Spurs last season, and Postecoglou revitalised the South Korea star during his debut campaign in the dugout. However, the 32-year-old has often gone missing in big games recently - offering just one goal and one assist in his last eight Premier League matches.

Called a "leader" in the squad by Postecoglou, the former Bayer Leverkusen sensation hasn't exactly lived up to that tag lately, and GiveMeSport now report that he could even depart this summer - despite the north Londoners' decision to trigger his one-year contract extension clause.

Indeed, Tottenham are apparently thinking about selling Son this summer in a previously "unthinkable" move, with Levy, Postecoglou and the club's board weighing up a squad revamp this summer as the rebuild continues.

The winger has made over 400 appearances for Spurs, racking up 172 goals and 92 assists in that time, but they need his very best now more than ever.