Football London

Tottenham are continuing to look into the South American market for the next generation of stars with an approach for one of those set to be made in January

Tottenham are reportedly weighing up a January offer for young attacker Leonel Flores but Boca Juniors president Juan Roman Riquelme is adamant he is not leaving. Spurs were linked with a move for the 19-year-old during the final stages of the summer window but an exit during that trading period was ruled out.

The Lilywhites were also focused on other matters surrounding deadline day due to Kevin Danso's exit wish and a move for Iliman Ndiaye failing to go through. The former departed for Sunderland with Tosin Adarabioyo joining as his replacement and Mykhailo Mudryk also signing from Chelsea.

Though the previous transfer window has only just closed, focus has already switched to January, with Flores seemingly a target for that month. Argentine outlet El Intransigente, as relayed by Sport Witness, have claimed that Spurs are thinking about submitting a proposal in the next window.

It was previously stated that Tottenham was only interested in him but that prompted a clear response from Boca that he would not be leaving. However, the report also stated that Boca only did not want to sell in the summer and at the right price, could accept an offer next year.

That proposal will likely need to be steep but his release clause, which is said to be in the region of €13million (£11.3m), may make matters easier for Spurs. Flores is also under contract in Argentina until 2029.

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The teenager managed 19 goals and five assists in 51 matches for Boca’s reserves and has only recently moved to the first team. He has now played 14 times for the senior side, managing two goals and one assist.

Spurs have tried to sign exciting talent from abroad in recent years; Luka Vuskovic, Alejo Veliz and Souza are just a few examples with varying success. The latter duo both came from South America with Souza now on loan at Porto after joining earlier this year.

January 2025 transfer activity pales in comparison to the club's summer spending with Conor Gallagher being the other addition alongside Souza

Ahead of the 2026/27 season, Sandro Tonali, Mateus Fernandes, Savio, Jan Paul van Hecke and Tosin have all been signed on permanent deals. Omar Marmoush meanwhile, has joined on loan with a buy-obligation included while Mudryk has also joined on a temporary basis.

Marcos Senesi, Andy Robertson and Martin Dubravka are the free agents who have also joined. Several exits have also been sanctioned with Vuskovic, Cristian Romero, Djed Spence and Will Lankshear departing permanently.

Pape Matar Sarr, Guglielmo Vicario and Danso are just a few players to have gone elsewhere on loan. Spurs also decided against signing Randal Kolo Muani and Joao Palhinha after their loans last season.

Roberto De Zerbi boost as more of Tottenham's Premier League fixtures are confirmed  Football London

There are statistical anomalies, and then there is Tottenham Hotspur's relationship with penalty kicks.

That's if anyone associated with the club can remember what one of those is. The basic numbers are this: Spurs were last awarded a Premier League spot-kick away from home on May 13, 2023 - 1,216 days ago. The taker (and scorer)? A certain Harry Kane, who is now approaching the 150-goal mark with Bayern Munich.

Home penalties in the league have also become collectors' items, with the last one coming on May 25, 2025 - 473 days ago. Bizarrely, the Lilywhites have been given a decent number of spot-kicks in European competition, six since the end of November 2024.

The ludicrous wait for a Premier League penalty has left many fans wondering whether there is more to it than sheer bad luck, with many taking to social media to air their frustration and even suggesting a conspiracy against the club.

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One posted ruefully: "Fun fact of the day: Harry Kane has taken 50 penalties since Tottenham were last awarded one in the league away from home."

Another fumed: "These are the 'funny games' PGMOL like to play with Tottenham. It's just all 'joking around' when it's us." A third said: "This has to be an outlier that needs some explaining, surely?"

It's also been pointed out that Spurs have had five managers since their last domestic penalty away from home, while Micky van de Ven and Guglielmo Vicario have never been part of a Tottenham side awarded one while on their travels. To put it into context with worldwide events, Kane's 2023 spot-kick was awarded just a week after King Charles' coronation, while Joe Biden was still US president.

Spurs' detractors will cheekily point out that "you have to get near the opposition's goal to win a penalty" but that cheap shot doesn't stand up to scrutiny, according to stats provided by Opta.

Since Spurs were last given an away penalty, yo-yo club Burnley have been awarded three. Fellow relegated sides West Ham and Wolves have been given five and four respectively. Brentford lead the way with 10, ahead of predictable candidates Arsenal and Manchester City (both on nine). Next up on eight are Chelsea, Crystal Palace and Bournemouth.

Premier League away penalties given since Spurs were awarded one

Brentford: 10

Arsenal: 9

Man City: 9

Crystal Palace: 8

Bournemouth: 8

Chelsea: 8

Liverpool: 7

Newcastle: 7

Man United: 7

Brighton: 7

West Ham: 5

Fulham: 5

Leeds: 5

Nottm Forest: 4

Wolves: 4

Aston Villa: 4

Everton: 3

Burnley: 3

Sunderland: 3

Luton: 2

Leicester: 2

Spurs: 1

Ipswich: 1

Sheff United: 1

Southampton: 0

Coventry: 0

Hull: 0

Since Spurs' last home penalty, Newcastle and Brentford top the table with six, ahead of Chelsea on five and Bournemouth and Manchester United on four.

Again, it can't be argued that Spurs don't get in the box enough. Since the 2023/24 season, Tottenham have had 3,481 touches in the opponent's area. That is similar to Chelsea (3,421), Manchester United (3,305) and Aston Villa (3,118).

The most eye-opening stat is the number of touches in the box per penalty awarded. Spurs have had 580.2 touches in the area for every spot-kick, far more than any other side.

Next up are Everton (371.6), Southampton (364.0) and Ipswich Town (348.0). Remarkably, Chelsea have had just 136.8 touches in the box per penalty awarded, with only Leeds sitting below them on 119.0.

Touches in box per penalty awarded since 2023/24

Spurs: 580.2

Everton: 371.6

Southampton: 364.0

Ipswich: 348.0

Nottm Forest: 319.8

Aston Villa: 311.8

Burnley: 304.2

Arsenal: 270.1

Fulham: 267.7

Wolves: 258.0

Man City: 251.2

West Ham: 223.0

Leicester: 220.7

Liverpool: 204.4

Bournemouth: 199.3

Brighton: 193.3

Man United: 183.6

Luton: 166.0

Crystal Palace: 164.3

Newcastle: 161.2

Brentford: 155.4

Sunderland: 139.0

Sheff United: 139.0

Chelsea: 136.8

Leeds: 119.0

So Tottenham are getting in the opposition box, are looking dangerous and are creating chances. But how many more years will they have to wait for a penalty away from home?

Fans have every right to have raised their concerns - the stats don't lie.

Richarlison's Tottenham situation remains a mess with the striker considering legal options that could include ripping up his contract as the Brazilian transfer window edges towards its conclusion.

The 29-year-old is currently stuck in limbo at the north London club, having been left out of Roberto De Zerbi's 25-man squad for the Premier League so unable to play. Spurs could only name 17 non-homegrown players in the squad registered with the league, which cannot be changed until the next English transfer window.

De Zerbi told football.london that Richarlison has repeatedly asked to leave the club this summer, and the Italian duly selected Xavi Simons in his squad over the forward, despite the Dutchman facing further months out as he continues to undergo rehabilitation for the anterior cruciate ligament injury he suffered in April.

Richarlison and his camp are said to be exploring his legal options which could include lodging a request to terminate his contract after not being registered in Tottenham's Premier League squad, although there is an awareness that any such move would be difficult.

It comes amid links with the club he supported as a child - Vasco da Gama - before the Brazilian transfer window closes on Friday in his homeland.

The striker, who was Tottenham's top scorer last season and started their opening match at Brentford this season, has a contract until next summer, but the club have the option to add another year on top of that deal he signed back when he arrived in 2022 in a £60million transfer from Everton.

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He turned down a move back to his former club this summer as the finances were not right and was linked with a move to Trabzonspor that never materialised before the Turkish deadline.

Despite reports in his homeland that Richarlison has been placed with Spurs' U21s and De Zerbi appearing to suggest he was not training with his group ahead of Saturday's draw at Nottingham Forest, images from Tuesday have shown the striker has been training with the first team squad this week.

There are strict rules about 'bombing' players out of a squad nowadays which clubs are wary of after some high profile cases in recent years.

Richarlison could be in for a struggle to engineer a contract termination at this time early in the season. Article 15 of the FIFA Regulations on the Status and Transfer of Players, which explains when a player can end their contract early due to sporting just cause, states: "An established professional who has, in the course of the season, appeared in fewer than ten per cent of the official matches in which his club has been involved may terminate his contract prematurely on the ground of sporting just cause.

"Due consideration shall be given to the player’s circumstances in the appraisal of such cases. The existence of sporting just cause shall be established on a case-by-case basis. In such a case, sporting sanctions shall not be imposed, though compensation may be payable.

"A professional may only terminate his contract on this basis in the 15 days following the last official match of the season of the club with which he is registered."

Richarlison is said to prefer a temporary switch to Vasco until the winter but a loan move is off the table as Spurs have already reached their limit of six international loans out of the club.

Guglielmo Vicario, Pape Matar Sarr, Radu Dragusin, Souza, Kota Takai and Yang Min-hyeok all went out on loan this summer across Europe. The only exemptions allowed to the rule, under FIFA's regulations, are players aged 21 and under who are also club-trained, which means Mikey Moore's temporary switch to Koln does not count towards their limit.

That means Vasco, or any other Brazilian club, would need to sign Richarlison on a permanent basis to prise him away from north London. Official talks between Vasco and Tottenham over a transfer for the striker are understood to not currently be taking place and all eyes will now be on the remaining days of the Brazilian window.

Richarlison 'trying to tear up Tottenham contract' as dream club told to pay £20m  Football London

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Roberto De Zerbi continues to be hampered by Tottenham injury problems with a new issue emerging after some return boosts

Mykhailo Mudryk has joined James Maddison, Dejan Kulusevski and two others on Tottenham's injury list after suffering an ankle problem in training. The deadline day loan signing made his Spurs debut - and first competitive appearance in nearly two years - last Saturday in the goalless draw against Nottingham Forest.

However, he will have to wait at least four weeks to play in another match with the ankle sprain set to keep him out until after the international break, football.london understands. Maddison, meanwhile, is one Spurs attacker who will be hoping to return before the extended domestic pause.

He has not featured since suffering a shoulder injury on the opening day of the season but he is now back in training. Kulusevski has also stepped up his recovery by appearing in team training sessions but a return to action is not expected for some time with the Swede having not played since May 2025.

Long-term knee injuries are also what Wilson Odobert and Xavi Simons are recovering from. The latter may struggle to feature this season while Odobert has already missed seven months and could therefore be back before the end of 2026.

With all of that being said, football.london has taken a look at the latest updates on Spurs' injured stars and when they could return.

Mykhailo Mudryk

Mudryk will miss Tottenham's next three games against Everton, Liverpool and Aston Villa at the very least. Having missed such a large portion of time, it is perhaps no surprise that the Ukrainian has picked up a problem.

The best-case scenario is that he only misses a month or so but it is possible he is absent for as long as eight weeks, depending on how his recovery goes.

Possible return date: October/November.

James Maddison

Maddison has been extremely unlucky with injuries over the last 18 months and though his latest problem was a minor one, it caused him to miss three games.

The 29-year-old was back in training last Thursday but the trip to Nottingham Forest just came too soon. Assuming he has been able to get a full week of training under his belt, Maddison should be back in the squad for the visit of Everton.

Possible return date: Everton (H) - Saturday, September 12.

Dejan Kulusevski

Footage of Kulusevski in training emerged late last month which excited Tottenham fans, but the club are being extremely careful given how long he has been out.

And the need to do that was highlighted by De Zerbi revealing a small issue had halted his progress but that it would not keep him out for very long. Nonetheless, it will probably be a while before the 26-year-old is back in a squad.

What De Zerbi has said: "Kulusevski started with us in the beginning of the week, and then the last two days, a small, small problem, stopped, but I think he’s in a good way. It’s going very well.

"I already said the medical staff is very high level. So I think we can be positive with him. I’m looking forward to having Deki in the squad."

What Sweden boss Graham Potter said: "He is actually very close. I am so impressed with him, how he has handled his injury. Of course, we have to be careful with him. I hope he comes with us (Sweden), but we have to talk to Dejan and Tottenham first."

Possible return date: Late 2026.

Xavi Simons

Simons ruptured his ACL back in April and that will likely see him miss most of the current season. He has, however, been named in Tottenham's Premier League squad.

Possible return date: Spring 2027.

Wilson Odobert

Odobert suffered the same injury as Simons but is much further along on in his rehab having hurt his knee back in February. A return to action this calendar is certainly therefore possible given players usually recover in nine months.

Possible return date: November/December 2026.

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