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A "special" player is likely to leave his club in 2025, despite only just signing a new contract, and it is believed he could join Tottenham Hotspur.

Spurs' transfer plans for next year as Lange works behind-the-scenes

It has been a testing start to the season for manager Ange Postecoglou, with Spurs blowing hot and cold over their opening fixtures of the campaign.

Recently, Postecoglou's side went on an impressive five-game winning streak in all competitions, with Wales winger Brennan Johnson front and centre of it, as he enjoys quite a purple patch right now.

However, that run unceremoniously ended with a dramatic 3-2 defeat away to Brighton. Spurs were two goals up at half-time, but they ultimately capitulated at the Amex, with Yankuba Minteh, Georginio Rutter and Danny Welbeck cementing their fate.

"You never know if it [the international break] is good or bad. Maybe for the players it was good, but I don't like sitting on a loss," said Postecoglou on Tottenham's 3-2 defeat to Brighton.

"There can be a tendency to over-analyse things. It wasn't a good one. The first half was unbelievable, but I didn't like the second half and what we looked like. It wasn't the loss, it was the manner I wasn't comfortable with. I've been sitting on it for 10 days, I'm ready to explode once they get back in the building and that will be my therapy."

As Postecoglou unleashes on his current squad, just before they take on West Ham in a fierce London derby clash this weekend, technical director Johan Lange and the Lilywhites recruitment team are working to bolster the Australian's options in January.

Indeed, it is believed Tottenham are targeting Espanyol winger Javi Puado, with his deal set to expire next summer, so the La Liga side could be forced to cash-in on the cheap this winter. Spurs are chasing Shakhtar Donetsk attacking midfielder Georgiy Sudakov as well, as Lange and co weigh up alternative attacking midfield options to James Maddison.

Patrick Dorgu could join Tottenham despite new contract

Another rumoured target for Postecoglou's side is Lecce youngster Patrick Dorgu.

The Dane has been impressing in Serie A, with Dorgu attracting interest from Spurs among other elite Premier League sides. The teenage full-back recently penned a new deal with Lecce, committing his future to the club until 2029 and warding off potential suitors.

However, this apparently may not be the case, as Fiorentina News write that Dorgu is still likely to leave Lecce in 2025, with Spurs at the front of the queue for his services alongside London rivals Chelsea.

The fresh terms will hand Lecce an opportunity to garner more funds from Dorgu's departure, according to Fiorentina News, which means the north Londoners will have to pay more than his previously reported £25 million fee.

"You can just say that with some players it can go incredibly fast," said Denmark Under-21s coach Steffen Højer to bold.dk.

"He has already had a lot of playing minutes in Serie A with Lecce, and he has done really, really well. What is special about him is that he is a quiet and calm guy, but things are just incredibly natural for him on a football pitch.

"When he is put on a field, and it doesn't matter which team, he just fits in, and he just makes incredibly many good choices for such a young player He has clear qualities, and then there is a lot of work that needs to be done in relation to both being part of the U21s, but also eventually making the national team."

In recent months, Tottenham Hotspur’s activity in the transfer market has handed boss Ange Postecoglou the best possible chance of cementing the club’s place as a top-four Premier League side this season.

Since his appointment last summer, numerous key first-team members have been added, helping Spurs in their battle to secure consistent Champions League football in North London.

James Maddison joined the side in a £40m deal from Leicester City after their relegation to the Championship at the end of the 2022/23 season - with the midfielder enjoying a successful first 12 months under Postecoglou.

The Englishman has registered a total of 18 combined goals and assists since his big-money transfer, providing a huge attacking threat from a deeper position on the field.

Goalkeeper Guglielmo Vicario has also impressed after arriving last summer, nailing down the number one spot, making 49 appearances and keeping 11 clean sheets in the process.

However, despite the recent impressive signings from the club’s recruitment team, they have also enjoyed success in the transfer market during previous years, signing players who managed to have a huge impact on the first team.

Tottenham’s summer transfer window in 2015

After finishing fifth in the 2014/15 season, Spurs had the task of recruiting well during the off-season to push and secure a Champions League spot in the following season.

Owner Daniel Levy spent big that summer, forking out £22m for the signature of winger Heung-min Son from Bundesliga side Bayer Leverkusen - a bargain given his impact in North London since his transfer.

The South Korean star has since registered 164 goals in his 415 appearances for the Lilywhites, often being the player to create carnage in the final third after Harry Kane’s departure to Bayern Munich last summer.

Toby Alderweireld also arrived during the same transfer window, joining for only £11.5m from Atlético Madrid - in a move to help bolster Mauricio Pochettino’s backline.

The deal was undoubtedly a successful one, with the Belgian forming an excellent partnership with compatriot Jan Vertonghen and making 236 appearances during his six years in the capital.

However, another defensive reinforcement was added in the form of Austrian Kevin Wimmer, joining for just £4m from German side FC Koln on a five-year contract.

Undoubtedly, he was seen as one for the future but was unable to dislodge any of the aforementioned duo - restricting him to just 31 appearances at White Hart Lane.

He only lasted two years at the club, before he was sold to fellow Premier League side Stoke City in the summer of 2017 - a deal that proved to be an excellent one from a Spurs viewpoint.

Kevin Wimmer’s market value in 2024

His move to join the Potters saw Spurs bank £18m, subsequently making a £14m profit despite his lack of appearances - with his form at Stoke failing to demonstrate such a high transfer figure.

The now 31-year-old only managed 19 appearances under boss Mark Hughes, before three separate loan spells away from the Bet365 Stadium before eventually leaving the club in 2021 with the Potters now a Championship outfit.

Seven years on from his transfer away from North London, his market value has continued to plummet, with the Austrian now plying his trade for Slovak Bratislava in Slovakia.

He featured against Manchester City in the Champions League this season, but it hasn't stopped his decline in value, with Wimmer now only valued at £500k as per Transfermarkt.

It’s positive to see a former player finally looking settled after a torrid few years after a failed transfer, but from a financial perspective, the hierarchy certainly made the right call in selling the defender.

His lack of impact at Spurs made it a no-brainer to cash in on the Austrian defender, making a hefty profit on a fringe player - allowing for further investment in key first-team players down the line.

Former Tottenham Hotspur target Jack Grealish is a huge name in English football, coming through the Aston Villa academy, before captaining his boyhood club to promotion back to the Premier League during the 2018/19 season.

The midfielder amassed a total of 213 first-team appearances for the West Midlands outfit, making his breakthrough during a dark time for the club after multiple embarrassing performances on the pitch which resulted in their drop into England’s second tier.

However, his career could’ve been significantly different had he made the move to Spurs during the summer transfer window back in 2018, with the club reportedly making an offer for Grealish after their failure to win promotion from the Championship.

He didn’t exactly set the division alight, registering nine goal contributions in his 30 league appearances during the 2017/18 season, but it was enough for then-boss Mauricio Pochettino to lodge a £20m offer for the Englishman’s services.

However, Villa decided to reject it, standing firm on their £40m valuation of their homegrown talent, with Spurs subsequently missing out on a deal to sign the talented ace.

He would have undoubtedly provided added quality to the North London outfit, potentially transforming the forward line alongside Heung-min Son and Harry Kane - but ultimately it wasn’t meant to be.

Just a couple of years later, Grealish would make a big transfer away from Villa Park, but it wasn’t to join Spurs, subsequently strengthening one of their Premier League rivals in the process.

Jack Grealish’s time at Manchester City

After securing Villa’s survival on the final day of the 2019/20 season, Grealish would star in his final season at Villa Park, registering 16 goals and assists, leading to a huge transfer to join Manchester City.

Pep Guardiola’s side forked out £100m for his services - a record for an English player at the time before Declan Rice’s move to Arsenal - with the talent undoubtedly improving City’s already potent frontline.

Since his move in the summer of 2021, the winger has often struggled to cement his place as a regular, often having to settle for a place on the bench and potentially making a difference as an impact player.

His debut campaign at the Etihad saw him feature 39 times in all competitions, registering just six goals - a disappointing return after such a hefty fee was splashed out for his services.

However, it would be his best goalscoring season to date in Manchester, with the 29-year-old only notching a total of five and three goals respectively in his last two campaigns under Guardiola.

Despite his recent lack of goalscoring form at club level, he’s been given a chance to shine internationally under temporary England boss Lee Carsley - demonstrating that he’s a player who needs that belief and confidence in him to succeed.

The former Villa star has grabbed two goals in his three appearances under the interim manager, matching the tally he produced under former boss Gareth Southgate, for whom he featured 36 times.

Whilst he’s undoubtedly struggled to live up to the pressure of his £100m price tag, Grealish has still demonstrated that he’s capable of starring at the top level, having an abundance of quality in attacking areas.

Spurs will undoubtedly be kicking themselves for being unable to secure a deal for the winger a handful of years ago, with his rise nothing short of sensational and a credit to him for his determination to succeed.

However, after missing out on a deal for Grealish, many people at Spurs thought they landed their own version of the Englishman following the addition of one talent back in the summer of 2021.

The man who could have been Spurs’ own Grealish

Back in the summer of 2021, Spurs completed a deal to sign winger Bryan Gil from Spanish side Sevilla - with the Spaniard having real potential to succeed in the Premier League after his stint in LaLiga.

He made his debut at the age of just 17, enduring various loan spells away from his boyhood club, before moving to North London on a permanent deal.

Spurs forked out £21.6m for his services, with Argentine winger Erik Lamela moving to Sevilla as part of the transfer to take Gil to England’s capital.

Ahead of his transfer, The Mirror’s European Football Writer, Colin Millar, dubbed the Spaniard as a similar player to the aforementioned Grealish, with his direct dribbling ability comparable to that of the £100m man.

However, his move hasn’t lived up to expectations, only making 43 appearances for the Lilywhites three years after his big-money permanent transfer to the Tottenham Hotspur stadium, also failing to score a single goal in the process.

He’s subsequently been on three separate loan spells away from the club in recent times, joining former side Sevilla as well as Valencia, before linking up with Girona for the current campaign.

As a result of his lack of impact during his time in the Premier League, Gil has seen his market value plummet, further highlighting the club’s mistake in signing the 23-year-old.

Bryan Gil’s market value in 2024

Three years on from his move to Spurs, the winger has failed to pull up any trees, often looking below the level required for England’s top flight when featuring for the club - leading to his various loan spells.

His current stint will see him feature in the Champions League with Girona, giving him the platform to impress and potentially resurrect his disastrous last couple of years.

However, up to now, it appears he’s been unable to impress, with his market value way below the £21.6m fee that the North London side paid for his services a handful of years ago.

Gil is now only valued at £6m as per Football Transfers, a drop of over £15m since his transfer, with the club desperately needing to make a decision on his long-term future at the end of his current temporary stint away from the club.

It’s clear that after various spells in the first-team boss Ange Postecoglou doesn’t see the Spaniard as a member of his squad, which could lead to a permanent sale in the summer of 2025.

Gil currently has a contract in North London until June 2026, with next summer potentially the last chance to recoup as much of his transfer fee as possible.

Whilst his potential was there for all to see after his time at Sevilla, his move to Spurs simply hasn’t worked out for either party. From potentially being a £100m star in the making, the club have lost a lot of money on the youngster.

Given his recent slump in form and value, Daniel Levy and Co may have been better off completing a deal for Grealish when they had the chance in 2018, with the club left to rue their decision and forever wonder what could’ve been for the Englishman in North London.

Tottenham Hotspur and chairman Daniel Levy by extension are plotting a January bid to sign one prolific forward for manager Ange Postecoglou, coming as his club now consider selling mid-season, regardless of his star player status.

Spurs planning January transfers amid mixed start to season

Postecoglou promised supporters that he "always" wins trophies in his second season in charge, but so far, the chinks in Tottenham's armour have been exposed in a few Premier League matches this season.

Indeed, this was most apparent in their most recent top-flight encounter - a 3-2 defeat away to Brighton. Goals from Yankuba Minteh, Georginio Rutter and Danny Welbeck cemented a dramatic 3-2 comeback for the Seagulls, who were originally two down at half-time thanks to strikes from the in-form Brennan Johnson and playmaker James Maddison.

This ended Spurs' previous winning run of five games on the trot in all competitions, giving Postecoglou and club chiefs things to seriously think about after what the Australian called his "worst" defeat as Lilywhites boss so far.

"It was disappointing and I’m absolutely gutted with that," said Postecoglou.

"It's an unacceptable second half - we were nowhere near where we should be. Maybe we got carried away with how we were going. We kind of accepted our fate and it's hard to understand as we've not done that while I've been here. We usually fight for everything, and when you don’t you pay a price.

"Maybe things were travelling on too smoothly. Football and life will trip you up if you get too far ahead of yourself and that’s what it looked like in the second half. It’s a terrible loss for us, as bad as it gets, and there’s only one way to fix it and that’s my responsibility."

Tottenham take on West Ham United in a crunch London derby clash, their first game back after the international break, and Postecoglou will need to rally his side to a much more convincing performance than their trip to the Amex.

January represents a golden opportunity to strengthen Postecoglou's ranks as well, and they've already been linked with a few forwards. Spurs have their eyes on Espanyol winger Javi Puado, and an update has just come out of Spain on the matter.

Tottenham could make January bid for Puado

As per La Razon, Tottenham could make a January bid for Puado, as his contract is ticking towards expiry, and he may even be available for a cheap fee as a result.

Espanyol are considering a sale of the Spaniard, despite his star player status and the fact he scored 17 goals in all competitions for them last season. Puado boasts a further three goals from their opening eight La Liga games this campaign, starting the season off in fine fashion and attracting interest from England.

Jonathan David is a certified goal machine. Since joining Ligue 1 side LOSC Lille from Gent in the summer of 2020, the Canadian striker has scored 92 goals in 196 games. He's netted 26 in each of the last two seasons, and with 8 in 13 games already this term, he's again on course for yet another stellar campaign in front of goal.

Given his proficiency at putting the ball in the back of the opposition's net, it's no surprise that David, 24, has been continually linked with a move away from the Stade Pierre-Mauroy in recent years. Here's a rundown on who is currently sniffing around the £37.5m-rated star.

Arsenal

Arsenal have been perpetually linked with David since 2021. While their interest in signing the Canada international has yet to come to fruition, next summer could be when they finally land their man.

David will be out of contract and free to leave Lille, and according to Tutto Juve, the Gunners are ready to offer him a contract worth £96,000 per week in order to lure him to the Emirates.

Tottenham Hotspur

Arsenal aren't the only team from north London who want to get their hands on David. Tottenham Hotspur also reportedly want to land the forward, who, at just 24, is his national team's joint-top scorer of all time with 30 goals.

Spurs spent £65m to sign England international Dominic Solanke from Bournemouth in the summer, but so far this season, he's hit just three goals in eight games. BBC Sport fan writer Ali Speechly recently pleaded with Tottenham to "buy another striker or regret it".

"If we want to compete as a serious top-four team, we need a clear and consistent striker - or two," she wrote.

Newcastle United

Newcastle United's options up top are currently limited, with Alexander Isak and the ever-injured Callum Wilson the only two experienced strikers on their books. And with Wilson now 32 years old and in the final year of his contract, Tutto Juve claims that Newcastle are eyeing up David and are in the "front row" to sign him.

Meanwhile, according to GiveMeSport, the Magpies may try to sign David in January in a cut-price deal in the hope that Lille will accept the offer rather than run the risk of losing him for nothing at the end of the season.

Aston Villa

Aston Villa had contact with Lille over signing David this summer and, according to recent reports from Italy, will once again go in for the striker next year. According to transfer expert Fabrizio Romano, Villa didn't land David this year because "they could not find an agreement" with the player or Lille.

However, the French club will be out of the equation as of January, with David free to pre-negotiate with a new club in the new year, meaning Villa need only convince the striker himself that Villa Park is the place for him.

Angel Gomes' career so far has been quite the adventure. A Manchester United academy graduate, the English midfielder was released by the Red Devils in 2020 after being unable to make his mark in the first team. As a free agent, he was snapped up by Ligue 1 side Lille before being loaned out to Portuguese side Boavista.

After a stellar season in Iberia, he returned to Lille, where he has since been a regular starter for the six-time French champions. Now, not only is he an England international, but the 24-year-old is also attracting the attention of clubs from across the continent.

Manchester United

Realising they may have made an error in allowing Angel Gomes to leave the club, the Red Devils are now keen to bring him back to Old Trafford. That's according to GiveMeSport, which reported last month that United are "mulling over handing Gomes a chance to return" as he would count towards their homegrown quota.

According to GiveMeSport, United boss Erik ten Hag has told his scouting department to keep tabs on Gomes to see whether he can adjust to their style of play. However, if United did want to bring Gomes back, they'd have to give him a hefty pay rise, with the player reportedly looking to earn somewhere in the region of £150,000 per week. Gomes has previously said that he one day would like to return to Old Trafford.

"Do I imagine myself coming back one day? Obviously, it’s home. I would love to come back, but you never know in football," he told L’Equipe last year. "I just have to keep my feet on the ground, and keep playing, making the most of it. I can’t predict what will happen in the future."

Liverpool

According to a report from TEAMtalk, Liverpool sent scouts to watch Gomes in action last month. They reported that Liverpool's chief executive of football, Michael Edwards, sent representatives from Anfield to watch Gomes in Lille's 1-0 defeat at Saint-Etienne as they continue to consider a January move for the midfielder.

Should he join Liverpool, Gomes would become the 13th player to have played for both United and the Reds, joining the likes of Michael Owen, Paul Ince, and Peter Beardsley.

Tottenham Hotspur

According to GiveMeSport, Tottenham are seriously considering a move for Gomes. It was claimed last month that Spurs want to offer the 24-year-old a "route back to his homeland" and hope that they can negotiate a low-cost deal with Lille in January due to the midfielder's contract expiring in the summer.

Last summer, Spurs allowed three deep-lying midfielders to leave in the form of Oliver Skipp, Tanguy Ndombele and Pierre-Emile Hojbjerg, but only signed one player in the same position - that being Archie Gray, who they splashed £40 million on to bring in from Leeds United.

Manchester City

Few players in history have ever dared to cross the divide by representing Manchester United and Manchester City. According to TBR Football, City are hoping Gomes will soon be one of theirs.

It was reported in early October that the Sky Blues had joined the race to sign Gomes, with the club eyeing the Englishman as a long-term replacement for Ilkay Gundogan, who turns 34 at the end of October. Former United midfielder Nicky Butt said last month that Gomes is so good, he "could play for City tomorrow".

Newcastle United

Gomes is thought to be Newcastle United's top target for January. Reports relayed by Caught Offside stated in September that Magpies boss Eddie Howe is gearing up to make a move for the Lille star in the new year. However, while interested in Gomes, Newcastle do have "reservations about his size and slight frame", according to recruitment expert and former United chief scout Mick Brown.

"He’s always been a talent, when he was at [Manchester] United as a kid, he was impressive at every level, but there were always question marks about his physicality," Brown explained to Football Insider. "That’s why United let him go, but he’s gone abroad and been really impressive. I think French or Spanish football suits Angel more than the Premier League."

Aston Villa

Aston Villa are the most recent Premier League club to be linked with Gomes, with GiveMeSport reporting that Unai Emery's side have joined the race to sign the England international.

If he was to join Villa, Gomes would be reunited with fellow midfielder Amadou Onana, whom he played alongside for Lille during the 2021/22 season. Onana left Lille to join Everton before moving to Villa in the summer for a fee of £50m.

Tottenham Hotspur have a "really exciting" teenager who could be about to replace long-serving defender Ben Davies, with the former Swansea City star potentially playing out his final season in north London.

Ben Davies nearing Spurs exit after 11-year stay

Next summer will mark 11 years at Spurs for Davies, following his move to N17 from Swansea in 2014.

Since making the switch to London from Wales, the versatile defender has made an impressive 333 appearances in all competitions for Tottenham, playing in some huge games for the club and showcasing real reliability.

However, the 31-year-old is now reaching the twilight phase of his career and has barely been called upon by Ange Postecoglou so far this season. Davies captained Spurs to a dramatic 2-1 win over Coventry City in the EFL Cup, whilst also starting both of their Europa League games, but he hasn't played a single minute of Premier League football.

Davies didn't even make the matchday squad for Spurs' most recent top-flight clashes against Brentford, Man United and Brighton, with the centre-back/left-back reduced to being a bit-part cup player.

It is believed that Davies earns more than both Destiny Udogie and Micky van de Ven at Tottenham, despite the latter pair's status as mainstays in Postecoglou's starting eleven, so chairman Daniel Levy and technical director Johan Lange may well opt to let go of him when his contract runs out in 2025.

Luckily, Postecoglou appears to have a ready-made replacement for the veteran in summer signing Archie Gray. The 18-year-old can play in a variety of positions, including at full-back, so Gray may well stand out as a very good option to take Postecoglou's side forward in the coming seasons.

Gray is widely regarded as one of England's most promising up-and-coming talents, with Spurs utilising his quality on a number of occasions already following his stellar campaign at Leeds United in the Championship last season.

Tottenham tipped to replace Ben Davies with Archie Gray

Speaking to Tottenham News this week, pundit John Wenham has tipped Spurs to replace Davies with Gray. The former could be about to pass the torch down to Levy's summer signing, with Wenham also branding the teenager "really exciting".

“Gray is doing really well,” Wenham said.

“I think, at a minimum, he is going to become the next Davies in the squad, in terms of his reliability in multiple positions. Davies is out of contract this summer and I can see Gray taking his role in the squad. Him being so young and counting as homegrown too, that is really exciting.”

Leeds were heartbroken to lose their Thorp Arch academy graduate in the summer, highlighting just how highly rated he is by those working in the beautiful game.

"Understanding the attraction of Premier League and European football, the club, with a heavy heart, agreed the transfer, but the move has strengthened the board’s resolve to ultimately return Leeds to a position where it can meet the footballing ambitions of even its brightest stars," wrote Leeds in a candid statement (via Ben Jacobs).

"Whilst we understand that supporters will be hugely disappointed to lose such a home-grown talent, and a family name so synonymous with Leeds United, the move improves the club’s chance to compete for automatic promotion next season by increasing our ability to build a competitive squad within the league’s financial control regulations. Everyone at Leeds United is heartbroken to see one of our own depart and would like to thank Archie for all his efforts and professionalism."

Tottenham Hotspur have been the home to numerous attacking talents over the years, but they haven’t been able to help lead the club to a major honour.

The Lilywhites haven’t claimed a trophy since their League Cup triumph back in 2008, with boss Ange Postecoglou hoping to put an end to their torrid run during the current season.

He could be reliant on the likes of Brennan Johnson, with the Wales international currently enjoying the form of his life, scoring in each of his last six appearances for Spurs.

The former Nottingham Forest ace will be hoping to follow in the footsteps of compatriot Gareth Bale, who captured the hearts of everyone during his time in North London.

The flying winger scored 105 times in 251 appearances before securing an £85m deal to join Spanish giants Real Madrid during the summer of 2013.

He’s not the only player to produce phenomenal goal-scoring figures before departing to join a European giant to take his career to the next level.

Harry Kane’s stats at Tottenham

After coming through the club’s academy, striker Harry Kane had to bide his time before cementing his place in the first-team, eventually becoming one of the best-ever players in Spurs’ history.

The England international scored 280 times for his boyhood club, overtaking the legendary Jimmy Greaves as their all-time leading goalscorer - building a 60-goal gap in the process.

The 31-year-old moved to Bayern Munich last summer in a deal worth a reported £82m - leaving the club with a huge hole at the top end of the pitch, undoubtedly affecting their trophy ambitions.

Kane went on to enjoy the best goalscoring season of his career last season, registering 44 goals in as many games, but it wasn’t enough for Thomas Tuchel’s side to win the Bundesliga title - extending his wait for a trophy in his career.

However, he’s not the only goalscorer who left the club in recent years, with one player departing back in 2018.

The man who outscored Kane at Spurs

Striker Reo Griffiths was a product of the Tottenham academy, appearing to have a huge future at the club after his impressive goalscoring record at youth level.

The Englishman scored 33 times for the club’s U18 side during the 2017/18 season - a tally nearly more than double what Kane could manage at the same level.

Griffiths even scored four goals in a single game against bitter rivals Arsenal, prompting interest from some of Europe’s elite including Real Madrid and Barcelona.

As a result, the club offered the striker a professional deal to fend off interest from elsewhere, but he never ended up signing a new deal with Spurs - subsequently departing that summer.

He joined French side Lyon on a free transfer in 2018, only featuring for their youth sides and never making a senior appearance for the club despite all the promise he showed.

Griffiths would subsequently leave Lyon and join League One side Doncaster Rovers for an undisclosed fee, in a move to put his career back on track after his failed move away from North London.

Reo Griffiths' rapid decline since leaving Spurs

Six years on from his departure from his boyhood club, the striker is currently employed by MLS side Portland Timbers after two failed moves to multiple National League sides in England.

Griffiths made six appearances during a loan spell with Yeovil Town, before making a singular appearance for Wealdstone - failing to register a single goal in either of his respective stints.

He was subsequently released by Doncaster during the 2023/24 season, with the “excellent” finisher, as dubbed by analyst Tom Williams, eventually dropping as low as Sunday league side Critics FC to maintain fitness.

The now 24-year-old moved to Portland in April this year, joining up with their B-team in the third tier of American soccer, and is yet to make an appearance after suffering an Achilles injury just a month after joining the club.

It’s an unfortunate downfall for a once-promising player, with the youngster still having a huge chunk of his career left to turn around his flailing career.

The striker will remain as another case of what could’ve been if he had stayed at Spurs instead of a move to to Lyon - but his transfer is a stark reminder to any talent coming through that the grass isn’t always greener.

Tottenham Hotspur are a club desperate for some form of tangible success after failing to win a trophy since 2008.

Their move to the new Tottenham Hotspur stadium has allowed them to own one of the finest stadiums in the Premier League - hoping to attract some of the best talents in the world to the club.

The appointment of serial winner Ange Postecoglou tried to instil the winning mentality needed to compete at the top level, but they narrowly missed out on Champions League football during his first season at the helm.

He’s since shifted the club’s recruitment strategy to focus on younger talents to improve the first-team, whilst also hopefully making the club a hefty profit later on down the line - subsequently making them more sustainable.

However, the change in focus was needed, especially after the transfer window during the summer of 2020, which saw Spurs fork out some hefty sums on players not up to the level required in the Premier League.

Spurs’ transfer window in the summer of 2020

The COVID pandemic put a real impetus on spending money wisely given the lack of income due to the absence of supporters surrounding the restrictions around mass gatherings.

However, Spurs failed to do so during the aforementioned transfer window, splashing huge fees and unfortunately failing to gain their money's worth with their new additions.

Midfielders Giovani Lo Celso and Pierre-Emile Hojbjerg both arrived in North London, with the club paying a combined fee of over £50m for the duo.

A real expectation was placed on the shoulders of the pair to lead the side forward and take them to the next level - however, the moves never lived up to the hype with the club finishing seventh during their debut campaign in North London.

Just over four years on from their big-money moves, neither player remains at Tottenham, with Lo Celso now at Real Betis, with Hojbjerg plying his trade for Marseille in France.

However, despite their respective moves, one player who also arrived during the same window remains in North London and looks to be one of the worst signings in the club’s recent history.

Sergio Reguilon’s market value in 2024

Four years on from his transfer to the club under Jose Mourinho, left-back Sergio Reguilon still remains a Spurs player despite not featuring for the first team since the end of the 2021/22 season.

The 27-year-old has made 67 appearances for the club, following his £32m move from Real Madrid in 2020, but has failed to be the addition many expected him to be.

He infamously scored one of the most bizarre own goals in Premier League history, somehow finding the back of his own net after an attempted clearance against Aston Villa.

The Spaniard has since had loan spells away from London with the likes of Atlético Madrid, Manchester United and Brentford but has never demonstrated his quality enough for any of the sides to sign him on a permanent basis, with United presenter Beth Tucker dubbing the full-back as "awful" during his time at Old Trafford.

As a result of his lack of games for Spurs, his market value has massively plummeted, with the former Real Madrid star now only valued at £2.8m as per Football Transfers.

Reguilon has only been named in the matchday squad once this season, coming in the Carabao Cup victory over Coventry City, showcasing Postecoglou’s lack of trust in the Spaniard.

Given his lack of first-team action, he’s sat earning a living without having to lift a finger, with the club desperately needing to cut their losses and cash in on the 27-year-old.

It’s unfortunate to see such a highly rated player fail to make the grade, but unfortunately, his move has been a disaster and one that the club undoubtedly must regret.

Tottenham Hotspur have already "made a bid" to sign an attacking gem who's "flying" right now, with chairman Daniel Levy and the club's hierarchy attempting to build upon their long-term project with Ange Postecoglou.

Postecoglou endures mixed start to the season with Spurs

The Lilywhites appeared to have turned a corner before their dramatic 3-2 slump away at Brighton just before the international break, winning five games on the trot in all competitions, but their Amex defeat exposed the chinks remaining in Tottenham's armour.

Postecolgou's side were 2-0 up and cruising at half-time, and it looked at one point like they were set to extend their imperious winning run to six. Brennan Johnson continued his own exceptional run of scoring form with the opener against Brighton, with James Maddison doubling their lead just before the 40-minute mark, but a capitulation soon followed.

After the restart, and in the space of just 20 minutes, goals from Yankuba Minteh, Georginio Rutter and Danny Welbeck handed the home side a surprise 3-2 lead and brought attention to Tottenham's very questionable defending.

The defeat is Postecoglou's third of the season already, and they next take on arch rivals West Ham in a fierce London derby clash this weekend. Tottenham will need to respond in convincing fashion, or questions will continue to be asked about their hopes of winning silverware this season.

The January window could represent a chance to strengthen in key areas and boost Postecoglou's hopes of making good on his promise to end Spurs' 16-year wait for a trophy. It is believed Tottenham are eyeing an alternative playmaker to Maddison, with Skakhtar Donetsk star Georgiy Sudakov a target for them.

Meanwhile, there are claims Spurs could move for a new forward in January, leading to their interest in Espanyol star Javi Puado as they ponder a future without star man Son Heung-min.

Tottenham have "made a bid" to sign Mason Melia

Levy and technical director Johan Lange are also always on the lookout for rising stars, with Republic of Ireland talent and St. Patrick's Athletic striker Mason Melia firmly on their agenda.

The 17-year-old striker is in demand right now, courted by "5/6" Premier League sides, and Spurs are among them. That is according to Irish journalist Conor McEvoy, who wrote via his "Rep of Ireland player tracker" feed on X that Tottenham have "made a bid" for Melia.

"Spurs have made a bid for Mason Melia with the asking price for Melia a million euro," wrote McEvoy.

"There are 5/6 Premier League clubs in the race for Melia’s signature and I expect something to formalise in the next few months with the race heating up. Mason can’t leave until he turns 18 next September so we have still a lot more time to witness his magic at home."

The teenager is earning rave reviews for his performances back home, and St. Pat's teammate Aidan Keena shared just how impressed he is with the attacking sensation.

"We have a good run of form going," said Keena.

"There's good competition for places in the squad. Mason started and showed that against Waterford, he's flying, we can all see the player he can be, if everything falls right for him,” said Keena, astonished at how quickly Wicklow native Melia has bedded in.

“When I was 16 I was in the St Pat's U-19s. So it's brilliant to see him in the first team at 16. He knows how good he is and how good he can be, he has a good head on his shoulders. He's playing men's football, and it's not just his goals, his overall game is getting better and better. I am there to give him any advice he needs but he doesn't need much, it will be me asking him for advice now.”