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We highlight five left-wing targets that Tottenham Hotspur could explore ahead of the January window, following their recent nine-figure cash injection.

Tottenham Hotspur received a huge boost ahead of the winter window following the Lewis family’s £100 million injection.

A portion of that amount is set to be made available for transfers, with Vinai Venkatesham and Johan Lange set to lead the recruitment strategy in January.

With that in mind, here are five left-wing targets Tottenham could realistically pursue in January to bolster their attacking depth and add more balance to the squad.

Kevin Schade is a familiar face for Thomas Frank

Thomas Frank has already confirmed that preparations for the January transfer window are underway, with Venkatesham and Lange leading discussions behind the scenes.

This winter, Tottenham could explore options to strengthen the flanks, particularly on the left side, where there is currently no guaranteed starter.

Wilson Odobert, Mathys Tel and Brennan Johnson have all featured there at different points this season, yet none have made the position their own.

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Tottenham have been linked with Kevin Schade of Brentford, a player Spurs fans have described as a “baller”. Schade is a familiar face to Frank, having worked with him during his time at Brentford.

Since taking over at Tottenham, Frank has not yet reunited with any of his former players, with Bryan Mbeumo joining Manchester United and Yoane Wissa now at Newcastle United.

That could change this winter if Tottenham decide to make a move, although reports suggest a summer pursuit might be more likely. The German international has scored one goal in seven league appearances this season.

Tottenham could revisit deadline day star Ademola Lookman

Tottenham were keen to add more attacking depth right up until deadline day, and with a move for Savinho falling through, Ademola Lookman was seen as the reported alternative.

The Atalanta winger attracted interest from several clubs, not just Tottenham, but a deal never materialised as the Italian side were only open to a permanent sale rather than a loan.

Spurs could revisit a move for Lookman in January, although such a deal appears unlikely at this stage. Lookman would be a solid addition given his Premier League experience from his time at Fulham and Everton.

Tottenham have found success signing players familiar with English football, as seen with Joao Palhinha and Mohammed Kudus quickly adapting to Frank’s system.

Rafael Leao could be an expensive ace for Tottenham

It is rare for Tottenham to make a blockbuster signing in the winter window, which makes Rafael Leao a more ambitious option. However, Spurs are known admirers of the AC Milan winger, who has been linked with a move to north London in the past.

Leao has struggled for minutes this season due to a calf injury, but still managed to score in the Italian Cup after coming off the bench for just 17 minutes.

Tottenham would likely have to spend upwards of £70 million to sign Leao, with AC Milan valuing the Portuguese forward at around £100 million (€118 million).

While the move seems unlikely, Leao’s pace, flair and technical ability make him an ideal fit for the Premier League, and Tottenham’s growing financial power could see them test Milan’s resolve.

A surprise move for Jack Grealish next summer

Although this list focuses on January targets, Jack Grealish could be one for the summer. The England international, currently on loan at Everton, has rediscovered his form after a difficult spell at Manchester City last season.

Tottenham’s long-standing admiration for Grealish is well documented. The club were close to signing him in the past, and with his City future uncertain, the move could finally happen.

Everton took a chance on him in the summer after his falling out with City, and he has since earned the Premier League’s Player of the Month award for August.

Grealish is expected to be available for around £50 million next summer, and despite being 30, his recent resurgence could make him an appealing option for Frank. Joao Palhinha’s success at a similar age could serve as an encouraging example for such a deal.

Antoine Semenyo is Tottenham’s dream addition

Finally, Antoine Semenyo remains one of the most admired targets among Tottenham supporters. Many fans have even joked that the club should spend the entire £100 million cash injection on the Bournemouth forward.

Semenyo has made a flying start to the season, registering six goals and three assists in the Premier League.

Tottenham were in the race for Smenyo’s signature last summer, but the player chose to extend his contract at the Vitality Stadium for another five years.

The forward could have been available for around £70 million last summer, a figure that now looks like a bargain considering his current form.

Two highly-rated English youngsters have announced that they are leaving their club, and Tottenham are keen to snap up the duo ahead of their rivals.

Tottenham have had success with their teenage recruits over recent years, with Lucas Bergvall, Archie Gray and previously Pape Sarr, all becoming important players for the club.

It is no surprise that the club are looking to repeat the trick again. According to reports, Tottenham have tried to sign Archie Gray’s younger brother, Harry, who is also a product of the Leeds academy.

Those are not the only brothers that Spurs are trying to unite at Hotspur Way. It was previously reported that Tottenham are eyeing moves for Middlesbrough’s twin midfield starlets, and there has been a big development regarding their futures.

Tottenham push ahead with moves for Anton and Bailey Palmer

The players in question are Boro’s 16-year-old twins, Anton and Bailey Palmer, who are both highly rated midfielders and have both featured for England’s Under-17s.

In a post shared on social media, Anton confirms that he and his twin brother have both decided to leave the Riverside Stadium after eight years at the club’s academy.

His Instagram post reads: “After eight years at Middlesbrough FC, we have made the decision to leave the club. We thank everyone involved in developing us into the players we are today from the medical staff to the coaches. This club will forever be a part of us. We have made memories and friendships for life, but it is now time for us to start a new journey.”

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According to TBR Football, Tottenham have wasted no time in making a move for the pair, with the Lilywhites already submitting offers for the teenagers.

Spurs face plenty of competition for the Palmer brothers

However, TBR Football say that Spurs are not the only ones to make an offer. In fact, the outlet claims that all five other members of the ‘big six’ have also offered deals to the teenagers.

Additionally, other Premier League clubs, including Brighton and Hove Albion, are also thought to be in the race for the Palmer brothers.

The publication adds that the midfielders are expected to announce within the next week what their next landing spot will be.

Journalist Pete O’Rourke believes that one Premier League club may have an advantage over Tottenham Hotspur in the race for Bournemouth winger Antoine Semenyo.

Many Tottenham fans have called on the club to spend ENIC’s £100m cash injection on Semenyo, and they will be encouraged by recent reports about the winger’s future.

According to The Independent’s Miguel Delaney, Spurs have moved ahead of the competition in the race for Semenyo, with the Lilywhites looking to get the deal for the 25-year-old done in January.

However, Thomas Frank’s men will have to shatter their transfer record for the Ghana international, with Bournemouth reportedly valuing the Tottenham target at £75m.

Why Tottenham are not favourites to land Antoine Semenyo

Last week, it emerged that Man United and Liverpool are ready to challenge Spurs for Semenyo’s signature.

Journalist Pete O’Rourke has now predicted that more clubs will enter the race for the Cherries star, and he suggested that the Reds will have an advantage in the race, having poached former Bournemouth sporting director Richard Hughes.

When asked about Liverpool entering the race for Semenyo, O’Rourke told Football Insider: “Yeah, well, look, there’s no surprise that some of these biggest clubs in England are looking at Semenyo.

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“Liverpool, we know their links with Bournemouth through Richard Hughes, the sporting director, which might give them a big advantage over the other interested clubs.

“Manchester United showed some interest in Semenyo in the summer, and Tottenham Hotspur also showed a bit of interest as well. I’m sure Manchester City, Chelsea, Arsenal would all consider Semenyo, and Bournemouth are bracing themselves for interest in him.”

Semenyo deal not expected to go through in January

Over recent days, we have heard from some sources that Bournemouth are determined to hold onto their star man until the end of the season.

This has now been backed up by O’Rourke, who claimed that he sees Semenyo exiting the Vitality Stadium next summer rather than in the upcoming transfer window.

The journalist added about the winger’s future: “I don’t see a move happening in January just due to the price tag that it would take to get him out of Bournemouth.

“I think in the summer all those clubs will be looking at Semenyo, seeing if he could be lured away from Bournemouth. Bournemouth are expecting serious offers for the player come next summer, having done well to keep hold of him this summer and tie him down to a new contract.

“Opportunities to move away will come with those big clubs, obviously looking to draw from that chance to play at the highest level possible.”

Tottenham Hotspur are looking to secure the long-term future of one of their key players, with Vinai Venkatesham making it a key priority before the winter window opens.

Not many defenders in the Premier League possess the recovery pace of Micky van de Ven, with the Dutchman clocking the fastest speed in the division last season.

Tottenham have a top-class centre-back within their ranks, and it is vital they keep hold of van de Ven for the foreseeable future.

The Dutch defender still has three years left on his current deal, yet he earns a modest £50,000 a week, a figure that hardly reflects his growing importance within the Spurs squad.

Vinai Venkatesham makes Micky van de Ven contract a priority for Tottenham

Tottenham want Micky van de Ven’s new contract finalised before the New Year to avoid speculation surrounding his future, according to TBR Football.

Van de Ven has reportedly attracted interest from Real Madrid in recent weeks, while Chelsea and Bayern Munich are also said to be monitoring his situation closely.

Football journalist Graeme Bailey told TBR Football that Venkatesham has made securing van de Ven’s new deal one of his top priorities.

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He revealed: “I am told it is very much one of Vinai Venkatesham’s priorities to get him tied down before the New Year; they do not want Van de Ven’s name to become part of the centre-back talk that is already happening.

“Spurs know he is under contract until 2028, so in theory he cannot move, but they want to keep him happy, and Spurs know he is as good as anything in England or indeed Europe at the moment.”

Van de Ven’s fitness is crucial to Spurs’ season hopes

Given Micky van de Ven’s incredible pace, there is always a tendency for muscular injuries to occur, and his record from last season would certainly have given Thomas Frank a cause for concern.

However, the Dutchman looks stronger and fitter this term, having yet to miss a single Premier League or Champions League fixture.

Tottenham will be hoping that this new run of form is a sign that his injury issues are now firmly behind him, because if he stays fit throughout the campaign, Spurs’ hopes of achieving their season’s ambitions will be significantly boosted.

Paul Gascoigne remains one of the most adored figures in Tottenham’s rich history, and though his spell in north London was brief, his impact was unforgettable.

During his time at Tottenham Hotspur, Gascoigne produced countless moments that have become part of club folklore, including that thunderous long-range free-kick against Arsenal in the FA Cup semi-final.

The Englishman spent just three years in north London, and that was enough for Gascoigne to become a hero among the Tottenham faithful.

His impressive performances helped the club to FA Cup glory in 1991, a fitting reward for a player who gave everything to the shirt during his time in N17.

Paul Gascoigne reflects on his time at Tottenham

Gascoigne has been speaking on talkSport, where he opened up about his time at Tottenham and some of the moments that defined his spell in north London.

The former England international revealed how he often joked with teammates before matches, showing the playful side that made him such a larger-than-life character.

Speaking about his time at Spurs, Gascoigne said: “Tottenham was funny, I used to say to the guys, lads do us a favour before the game. I am really tired of getting man of the match every game, can someone do well today so I do not have to go upstairs again and get pestered?

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“Like I would say to the England players, do us a favour guys, just if you are tired give us the ball, I will keep hold of it for five minutes and then you can have it back. Just some of the things I used to say.”

Gascoigne reveals what inspired his confidence and creativity

The England legend was also asked about where his confidence came from despite playing against elite opposition at such a young age.

Gascoigne admitted that much of his inspiration came from watching legends of the game and trying to replicate their brilliance on the training ground.

He said: “I just, I never really, I used to watch the old Match of the Day when I was younger, you know, and I used to watch, I do not know, I watched Cruyff do that turn and I went I am going to try that.

“So I got the ball straight outside and practised straight away, and I just, I do not know, sometimes like some of the stuff I did on the pitch, I was like I did not know how I did it.

“And I would go back home and I would watch it on TV like the old Match of the Day and think God, how did I do that?”

On what kept him driven on the pitch, Gascoigne simply said: “Yeah, I do not know.”

Tottenham Hotspur supporters have plenty to get excited about after some eye-catching performances on international duty.

Tottenham Hotspur showed great faith in Mathys Tel this summer when they made his loan move permanent, despite a fairly unconvincing first six months at the club.

The young French forward has endured some difficult spells this season already, but having grabbed his first goal of the campaign for Tottenham against Leeds United, he has now entered a rich vein of form.

He is not alone in that regard, with France under-21 international Wilson Odobert also producing standout displays while away with the French national team.

Tottenham fans react as Mathys Tel and Wilson Odobert star for France under-21s

France under-21s faced Estonia under-21s in a recent Euro under-21 group stage qualifier, and Tottenham’s Mathys Tel and Wilson Odobert were both on the scoresheet.

Tel opened the scoring and provided an assist, while Odobert bagged a brace and an assist as France cruised to a 6-1 victory.

Tottenham fans have been left buzzing by the performances of their two youngsters, with many taking to social media to share their excitement.

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One fan wrote: “Tel and Odobert’s confidence going back to Tottenham will be high. Tel’s first full 90 minutes and he scored was Aston Villa.”

Another added: “That assist from Odobert 🔥.” However, not everyone was fully convinced, with one supporter commenting: “Everyone celebrating goal and assist against not only U21 but U21 from Estonia… the standards for this club are on the floor. These are supposed to be our main offensive players.”

Another fan said: “Let’s see some of these goals and assists against @AVFCOfficial this weekend for #Tottenham #COYS.”

One more added: “Tel is about to go on a generational run, trust. Has to play against Villa.” Another stated: “Need this connection brought over to North London 🔗,” while one fan concluded: “Both need to start against Villa.”

Spurs need more from Tel and Odobert

Tel and Odobert should be full of confidence after their impressive showing on international duty with France’s under-21 side, but Tottenham need more from the duo.

Tel has now managed three goals in his last three matches, the first time he has achieved such a run since joining Tottenham permanently in the summer.

Tottenham Hotspur could be involved in a transfer merry-go-round with a Serie A club as they and their London rivals have set their sights on a striker who has found the back of the net four times this season.

Richarlison has blown hot and cold for Spurs at the start of the season, while Randal Kolo Muani and Dominic Solanke have been sidelined with injuries.

This has led to suggestions that Tottenham are looking to add a number nine to their squad during the January transfer window.

A week ago, it was reported that Dusan Vlahovic’s representatives had offered the striker to Tottenham, and a new update has now revealed what the Lilywhites are thinking about a move for the Juventus striker.

Tottenham are competing with London rivals for Dusan Vlahovic

According to a report in Quotidiano Sportivo, even though Vlahovic has scored four times for the Bianconeri this season, his future remains up in the air.

The centre-forward is no closer to signing a new contract at the Turin club, and with his contract running out next summer, his agent has been working hard to find his client a new home.

The outlet says that Tottenham Hotspur and Chelsea have both tested the waters over a move for Vlahovic ahead of the January window. There is hope at Juventus that a Premier League club could submit a bid for the Serbian when the transfer window reopens.

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Vlahovic could replace Randal Kolo Muani at Spurs

Quotidiano Sportivo suggest that the 25-year-old striker is being viewed as a potential replacement for Randal Kolo Muani by Tottenham.

It is pointed out that the North London side does not have the option to sign the Frenchman permanently, and it is asserted that the PSG man is still interested in a permanent switch to Juve, having spent the second half of last season on loan at the Serie A club.

The latest news coming out of an EFL club could hand a lifeline to Tottenham academy starlet Jamie Donley, who has struggled for game time at the start of the season.

Some Tottenham youngsters have been setting the stage alight in their loan spells at the start of the season, none more so than Luka Vuskovic, who is posting mind-blowing numbers at Hamburg so far.

However, other Spurs youngsters have not had the expected impact away on loan, with perhaps the biggest disappointment being the situation of Jamie Donley at Stoke City.

After Donley’s incredible exploits on loan at Leyton Orient last term, Tottenham fans were eagerly waiting to see how the attacking midfielder would do in the Championship, but things have not gone according to plan so far for the 20-year-old at the Bet365 Stadium.

Has the luck just turned for Tottenham youngster Jamie Donley?

Donley has not started a single Championship game for Stoke so far this season, having seen just 49 minutes of league football so far.

However, Potter’s boss Mark Robins may soon have to hand the Tottenham youngster a run of matches after the latest injury development.

Stoke’s main number ten, Bae Jun-ho, who has started nine Championship games so far this season, is now out with a dislocated shoulder.

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This could potentially hand Donley a chance to impress over the coming weeks and show Robins what he can do.

Donley can take inspiration from last season

It is worth remembering that the Spurs academy graduate did not have the best of starts to his loan spell with the Os last season.

Donley never looked back after he broke into the team, and the youngster will believe that he can do the same at Stoke.

It may only be October 2025, but Tottenham already have one piece of transfer business planned for the 2026 summer window.

Just as expected, Joao Palhinha has hit the ground running since his loan switch from Bayern Munich to Tottenham Hotspur in the summer.

Palhinha is currently leading the Premier League for tackles per 90 minutes, which will not come as a surprise to anyone who watched him during his Fulham days.

Reports over recent days have suggested that Tottenham are expected to take up the £26m option to sign Palhinha permanently, and now, a reputed source from Germany has provided an update.

Tottenham midfielder Joao Palhinha is unlikely to return to Bayern Munich

Sky Sports Germany reporter Florian Plettenberg has now become the latest to confirm that the Lilywhites are open to triggering the £22m-£26m option to buy the Portugal international.

Plettenberg explains that Thomas Frank has a very good relationship with the midfielder, who now appears unlikely to return to the Allianz Arena.

The journalist adds that while talks over a permanent move have not been held between the two clubs yet, the player is happy at his new surroundings and the deal is moving towards a ‘positive trend’.

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Could Spurs begin Palhinha talks earlier than expected?

Palhinha has admitted that he is now going through a ‘happy phase’ at Tottenham, and is enjoying football again as he feels the trust of the manager.

Some sources have claimed over recent weeks that Spurs could start talks with Bayern over a deal for Palhinha in January rather than wait until the end of his loan spell in the summer to activate his clause.

Tottenham boss Thomas Frank has identified a Premier League midfielder who will make a great coach or manager when he eventually hangs up his boots.

Frank has a reputation for being meticulous when it comes to tactical details, and one can already see the big change in how Tottenham Hotspur are set up this season.

The Spurs players have admitted that they now know exactly what to do in and out of possession, which perhaps was not always the case last season under Ange Postecoglou.

It is thus interesting to hear the Tottenham boss’ take on which player he expects to be a future manager, and he did not pick one of his players.

Tottenham boss Thomas Frank backs Man City star to become a future manager

We know that Ben Davies is working on his coaching badges, with the experienced Spurs defender having his sights set on getting into coaching when he hangs up his boots.

However, Frank believes that midfielders would be ideally suited to getting into management due to their understanding of the game, with the Dane picking Man City star Rodri as someone who could have success as a coach.

When asked which Premier League player would make the best future manager, the Tottenham boss told Sports Bible: “That was a very tricky, very tricky question, yeah. It needs to be a midfielder, I think, because normally it’s those who most normally become managers. I will name Rodri from [Man] City.

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“Clever midfielder, so maybe he’ll be a coach or manager one day. Yeah, I think he’s intelligent on the pitch. I think he’s also quite intelligent in the press, so yeah, if he wants to go into that circus.”

Frank would not recommend going into coaching

The Tottenham boss has now been a coach for nearly two decades since starting with the Danish youth sides and knows what it takes to work his way up to the top of the game.

However, Frank is not quick to recommend management as a career for players when they hang up their boots.