Chelsea’s potential outgoings could dominate transfer deadline day with speculation over Conor Gallagher and Armando Broja’s futures at the club yet to subside.

West London rivals Fulham have been linked to Broja over the last few days of the January window, while England midfielder Gallagher has been linked with a move to Tottenham throughout the month.

Spurs have been one of the busier clubs in a seemingly quieter January transfer window so far, with Radu Dragusin and Timo Werner arriving in north London, but head coach Ange Postecoglou suggested on Tuesday it would be “unlikely” to see any more signings

Financial services firm Deloitte suggested that clubs’ desire to avoid tough sanctions for financial rule breaches could be a factor in a general drop in Premier League transfer spending this month, but did not rule out a “late flurry” of activity before the 11pm deadline on Thursday.

Aston Villa have been active in the final stages of the window, with winger Morgan Rogers expected to join from Middlesbrough in a deal worth £16million.

Forward Jhon Duran has been linked with Chelsea, while Unai Emery is also keen to keep hold of Jacob Ramsey, who has been linked with Tottenham and Bayern Munich.

Speaking about the midfielder at a press conference on Monday, Emery said: “Jacob Ramsey is a very important player. He grew up in the academy and his progression is getting better.

“His level is increasing a lot and I want to keep him here with us. Of course, there are movements (speculation) around him.

“Maybe there are teams involved in the possibility to sign him because he has a big, big potential at Villa and in England. I want to keep him here, 100 per cent.”

Newcastle were another club linked with Ramsey, but Eddie Howe insisted on Monday that the Magpies had made no approach for the 22-year-old.

Howe added he is determined to keep his squad “intact” amid speculation over the futures of Kieran Trippier, Callum Wilson and Miguel Almiron throughout the window.

After securing Kalvin Phillips on loan, Portuguese winger Jota is reportedly a target for West Ham to replace Algeria winger Said Benrahma, who is likely to leave before deadline day.

Pablo Fornals could be another player to leave the Hammers and he is reportedly close to sealing a move to Real Betis.

Brighton have been linked with a move for Leicester midfielder Kiernan Dewsbury-Hall, but Seagulls boss Roberto De Zerbi remains tight-lipped about the speculation.

“I don’t know anything about him (personally); I know him as a player,” he said.

“He has great quality but it’s not my business speaking about other players, especially because (Foxes boss) Enzo Maresca is my friend and I want to be correct with him.”

There could be activity towards the bottom end of the Premier League table as Sheffield United boss Chris Wilder admitted the club will be working “frantically” to improve their squad before Thursday, while Nottingham Forest manager Nuno Espirito Santo is also hoping to bring in reinforcements.

Chelsea’s potential outgoings could dominate transfer deadline day with speculation over Conor Gallagher and Armando Broja’s futures at the club yet to subside.

West London rivals Fulham have been linked to Broja over the last few days of the January window, while England midfielder Gallagher has been linked with a move to Tottenham throughout the month.

Spurs have been one of the busier clubs in a seemingly quieter January transfer window so far, with Radu Dragusin and Timo Werner arriving in north London, but head coach Ange Postecoglou suggested on Tuesday it would be “unlikely” to see any more signings

Financial services firm Deloitte suggested that clubs’ desire to avoid tough sanctions for financial rule breaches could be a factor in a general drop in Premier League transfer spending this month, but did not rule out a “late flurry” of activity before the 11pm deadline on Thursday.

Aston Villa have been active in the final stages of the window, with winger Morgan Rogers expected to join from Middlesbrough in a deal worth £16million.

Forward Jhon Duran has been linked with Chelsea, while Unai Emery is also keen to keep hold of Jacob Ramsey, who has been linked with Tottenham and Bayern Munich.

Speaking about the midfielder at a press conference on Monday, Emery said: “Jacob Ramsey is a very important player. He grew up in the academy and his progression is getting better.

“His level is increasing a lot and I want to keep him here with us. Of course, there are movements (speculation) around him.

“Maybe there are teams involved in the possibility to sign him because he has a big, big potential at Villa and in England. I want to keep him here, 100 per cent.”

Newcastle were another club linked with Ramsey, but Eddie Howe insisted on Monday that the Magpies had made no approach for the 22-year-old.

Howe added he is determined to keep his squad “intact” amid speculation over the futures of Kieran Trippier, Callum Wilson and Miguel Almiron throughout the window.

After securing Kalvin Phillips on loan, Portuguese winger Jota is reportedly a target for West Ham to replace Algeria winger Said Benrahma, who is likely to leave before deadline day.

Pablo Fornals could be another player to leave the Hammers and he is reportedly close to sealing a move to Real Betis.

Brighton have been linked with a move for Leicester midfielder Kiernan Dewsbury-Hall, but Seagulls boss Roberto De Zerbi remains tight-lipped about the speculation.

“I don’t know anything about him (personally); I know him as a player,” he said.

“He has great quality but it’s not my business speaking about other players, especially because (Foxes boss) Enzo Maresca is my friend and I want to be correct with him.”

There could be activity towards the bottom end of the Premier League table as Sheffield United boss Chris Wilder admitted the club will be working “frantically” to improve their squad before Thursday, while Nottingham Forest manager Nuno Espirito Santo is also hoping to bring in reinforcements.

Tottenham head coach Ange Postecoglou does not predict Liverpool or Manchester City falling away in the coming years irrespective of who manages both clubs.

City have won five of the last six Premier League titles with current leaders Liverpool breaking the monopoly in 2020, but Jurgen Klopp will depart Anfield at the end of the campaign.

Klopp will leave after nine seasons in England and Pep Guardiola will match that tally next term.

Postecoglou has repeatedly expressed his desire for Spurs to regularly compete with the best clubs in England, but knows they must improve and not rely on others to dip in order for that to happen.

“If that’s your only hope, waiting for the top ones to slip? I just don’t think you get there. I really don’t,” he said ahead of Brentford’s visit on Wednesday.

“I’d rather them be at their best and we match them, get up to their level and exceed it. Rather than hope they slip up. I just don’t think that’s a strategy. It is more of a wish.

“We got a real good indicator the other night and to be fair to the lads we hung in there, fought hard but we were playing against probably the best side in the world at the moment and there was a difference between us, for sure.

“If we’re hoping they will come back to us, rather than us try to get to them, you’re chasing a lost cause.

“I just don’t see them coming back to the field. Even with Jurgen going, I still think there is a really strong squad there, a really strong mentality.

“I’ll be very surprised if whoever takes over doesn’t continue to build on that.

“I always think with those kind of things, it’s up to the challengers to change the status quo. That can only happen if you have that sort of desire and will to challenge that and not be afraid of falling short, because ultimately if you don’t, they’re just going to keep winning.”

What may help Tottenham’s cause is the growing revenue streams at the club after they were placed eighth in last week’s Deloitte Football Money League.

It makes Spurs the richest club in London with a revenue of £549.2million in the 2022-23 season.

But Postecoglou insisted: “It helps and it’s a credit to the club we got ourselves in that position, but that’s not what clubs are measured by. They’re measured by other things.”

The Australian was also guarded on whether this quiet January transfer window is a sign of things to come.

He added: “Hard to say if this is the New World. Obviously there’s financial parameters dictating how these windows work.

“Maybe the way clubs are working is sort of changing. I think there are more strategic decisions and less not panic buys, but desperation just to bring anybody in, or just buy someone.

“I think clubs are being a little bit more strategic now in these moves. I also think there’s very little secrets out there.

“If you went through all the Premier League clubs and snatched their list of 18-21 targets, I don’t think there would be a lot of difference between them all.

“Everyone’s a little bit more cagey and strategic. Will it last? Maybe. I don’t know, but that’s certainly the indication I get at the moment.”

Tottenham head coach Ange Postecoglou expects a quiet last few days of the January transfer window.

Spurs have been one of the most active clubs this month, with Radu Dragusin and Timo Werner arriving and several other players finding new loan teams.

Talks had started with Club Brugge over the signing of highly rated attacker Antonio Nusa, but no fee could be agreed and it appears the club’s business is done ahead of Thursday’s deadline.

“Look, unlikely I’d say. I don’t see any incomings,” Postecoglou said at his pre-match press conference ahead of Wednesday’s Premier League game against Brentford.

“Outgoings, a little bit different because I’m not totally engaged with that. Other people are doing the work around that.

“I’d say unlikely on both fronts, without ruling anything out.

“I’ve enjoyed working with (technical director) Johan (Lange) and his team. I am sure going into the summer we’ll be in a good place to make sure we again try to take advantage of the fact we can make our squad and team stronger for what is ahead.”

Spurs will aim to bounce back against Brentford after exiting the FA Cup on Friday night following a 1-0 loss at home to Manchester City.

It means the club’s trophy drought is set to extend into a 17th year unless they can win the title this season.

Postecoglou added: “It’s disappointing we’re out of both cup competitions, particularly with not being in Europe because obviously the supporters are really crying out for some sort of success to experience at this football club, but I can’t let that guide my course.

“This is still about us growing as a team and finishing the second half of the season stronger than the first.

“If we do that, we’ll be in a good position to continue to challenge and push this team along. That’s our focus.

“As much as there’s disappointment that we’re out of another cup, there’s also a reminder to us that it’s not just about winning one trophy. If we’re going to compete at that level we want to, then we’ve still got a lot of work to do.”

James Maddison could start on Wednesday after he made a cameo off the bench against City in his first appearance since being ruled out for close to three months with an ankle injury.

Tottenham will remain without Pape Sarr, Yves Bissouma and Son Heung-min due to international commitments, but Sarr will return on Wednesday after Senegal were knocked out of the Africa Cup of Nations on Monday and could be available for Saturday’s trip to Everton.

Postecoglou also confirmed Manor Solomon has suffered a setback on his return from a knee injury.

What the papers say

Conor Gallagher could make a move across London as the end of the January transfer window looms. According to The Times, Tottenham are weighing up a potential bid for Chelsea’s England midfielder, 23.

Manchester United winger Facundo Pellistri, 22, could be heading for a spell away from Old Trafford. Spanish club Granada have revived plans for a loan move for the Uruguay international, reports the Manchester Evening News.

West Ham have turned their attention to Portuguese winger Jota, 24, from Al-Ittihad, according to the Evening Standard. Hammers talks with FC Nordsjaelland over Ghanaian forward Ibrahim Osman, 19, have stalled.

Leeds have made an offer to Everton for Ben Godfrey, reports The Sun. The Championship club are looking to take the England international defender, 26, on loan.

Social media round-upPlayers to watch

Jacob Ramsey: Newcastle, Tottenham and Bayern Munich are interested in the 22-year-old midfielder, with Aston Villa considering a sale to comply with financial regulations, reports The Athletic.

Chuba Akpom: Everton and Luton are keen on signing the English forward, 28, on loan from Ajax, says Teamtalk.

Christian Eriksen signed for Inter Milan from Tottenham for a fee in the region of £17million on this day in 2020.

The Denmark international joined Inter on a four-and-a-half-year deal following six-and-a-half years with Spurs, where he scored 69 goals and provided 89 assists in 305 appearances.

Following his departure, Eriksen posted on X, formerly Twitter: “Dear Tottenham fans, I don’t know where to start!

“I didn’t have time to say goodbye to everyone, even though I felt like I played a lot of games where everyone said and thought I would be gone the next day.

“I have so many unbelievable memories over the last 6.5 years I was at Spurs.

“I enjoyed being at the training ground every day and playing games in the stadium so much, but sometimes you just want to try something new.

“So, Spurs fans it has been a pleasure to play at your club and hopefully we meet again in the future.”

Eriksen won a Serie A title with Inter, but left the club in December 2021 after suffering a cardiac arrest at Euro 2020 during Denmark’s opener against Finland.

After receiving life-saving treatment on the pitch, he was taken to hospital and fitted with an implantable cardioverter defibrillator (ICD) device.

Serie A rules stated that Eriksen would be unable to play with an ICD and an agreement was struck for him to leave.

He then signed for Brentford on a six-month deal in January 2022 before joining Manchester United that summer.

Nathan Ake admitted to a sense of relief that Manchester City finally broke their Tottenham Hotspur Stadium curse to stay on track to defend their FA Cup crown.

The holders squandered a number of chances in Friday’s fourth-round tie at Spurs before Ake poked home from close range with two minutes left.

It represented City’s first goal at Tottenham’s new home at the sixth time of asking and the centre-back conceded it felt like being another night to forget until his timely intervention.

“So happy. It was tough but we played really well over the whole game. We just had to score and it didn’t happen again for a long time. I was thinking is it going to happen but luckily we got it,” Ake said.

“I think trusting the way we played (was key). We played really well, created numerous chances and just the belief to keep going. Even though we didn’t score, just to keep going, keep trying and in the end we got it.

“I thought it is never going to come but finally we’ve done it.”

The introduction of Kevin De Bruyne proved crucial and it was his corner which created Ake’s 88th-minute winner.

De Bruyne had been left red-faced six minutes earlier when he curled wide with only Guglielmo Vicario to beat, but made amends with an exceptional set-piece delivery.

The 1-0 win made it seven victories in a row for City, who remain in the hunt for another treble after claiming Premier League, FA Cup and Champions League success last season.

Ake told ITV: “I think it was important to go through, we want to fight for every competition and this was a big step forward.”

Following a lacklustre first half, all eyes were on when De Bruyne and fit-again Spurs playmaker James Maddison would get the nod to come on.

Maddison made his first appearance since he sustained ankle ligament damage on November 6, but only touched the ball six times as Tottenham struggled to gain a foothold in the contest.

Spurs boss Ange Postecoglou hoped Maddison would be better for his 17-minute cameo with games to come against Brentford and Everton next week.

“Knowing the nature of the game, he’s trained well this week-and-a-half but he’s missed a lot of football,” Postecoglou explained.

“We were hoping to get him some minutes, which he did and he should be right to go from now on, but there’s another two games next week and we need him and others to pitch in.

“So, yeah it wasn’t really much of a dilemma about whether to start him or not. I just felt that coming off the bench was going to be better for us as a team more than anything else.”

Pep Guardiola lauded an unbelievable performance from his Manchester City side after they ended their Tottenham Hotspur Stadium goal drought with a narrow 1-0 away win.

City had failed to score in their previous five trips to Spurs’ home and an FA Cup fourth-round replay looked on the cards when substitute Kevin De Bruyne inexplicably fired wide from 16 yards with eight minutes left.

The breakthrough did finally arrive for the visitors with 88 minutes on the clock when Guglielmo Vicario flapped at De Bruyne’s corner with Ruben Dias in close proximity and Nathan Ake poked home from close range to end the FA Cup holders barren run at Tottenham.

“Deserved it? I think so but football is about scoring, not conceding and the statistics were really good today,” Guardiola explained.

“If you see the stats from the past when we come here, we could not score and could not win.

“Yeah, we are really pleased of course to win against this team away, score a goal and go through. We defend the title and the way we play, we proved we defend it really well.

“Unbelievable. The performance was top, top class. These players prove again the reason why they have done what they have done in the past.”

City had the ball in the net after five minutes but Oscar Bobb was adjudged to be marginally offside after Vicario had thwarted Foden from close range.

Spurs barely had a kick in the first half and while Brennan Johnson was denied by Stefan Ortega at the start of the second period, it proved the hosts’ only shot all match.

Guardiola’s team continued to press for their maiden goal at Tottenham’s stadium and after Bernardo Silva, De Bruyne and substitute Jeremy Doku all failed to make the most of promising situations late on, Ake produced the goods with two minutes left.

It was a dangerous delivery from De Bruyne which caused panic in the Spurs box on only his third appearance since his lengthy lay-off following a serious hamstring injury sustained last season.

Asked if De Bruyne was fit enough to start, Guardiola said: “He is ready. Ready to play.

“Sooner or later he will play from the beginning, but it’s not just about that. For many reasons we want to protect him and Kevin, today I always knew he was going to create.

“These type of games at the end, it was a little bit more open and we had that feeling. It is important he feels good after his hamstring problem and he made an exceptional corner in the right spot. We knew it, so yeah it’s really good.”

Guardiola also reflected on the news on Friday morning that great rival Jurgen Klopp will leave Liverpool at the end of the season and dispelled any talk that he could follow suit.

“I am fine. Still one more year I want to do it and maybe extend (past 2025), so I am fine,” Guardiola insisted.

Meanwhile, opposite number Ange Postecoglou cut a frustrated figure after Spurs exited the FA Cup following a lacklustre display, which will all but ensure the club’s trophy drought will extend into a 17th year.

Postecoglou admitted: “We fought hard to stay in the game but to be honest that’s all we did, we stayed in the game.

“They’re a top team. They’re the benchmark. We’re not there yet and we’re under no illusion about that.

“I just felt that all of the second half was ok, the first half we were just too passive in a lot of our play and allowed them to get a rhythm.”

Nathan Ake’s 88th-minute tap-in helped Manchester City end their Tottenham Hotspur Stadium hoodoo and progress into the FA Cup fifth round after a 1-0 away victory.

Pep Guardiola’s side had failed to score in their previous five visits to Spurs’ home and that unwanted record looked set to extend until Ake bundled home from close range after Guglielmo Vicario flapped at Kevin De Bruyne’s corner.

All eyes had been on De Bruyne and Tottenham playmaker James Maddison after a lacklustre first half and while the former helped break the deadlock, it was an uncharacteristic City goal that fired them to a seventh straight win.

Ange Postecoglou’s team could have little complaints and this cup loss means the club’s trophy drought will almost certainly extend into a 17th year.

These teams had played out a 3-3 draw at the Etihad last month, but both the club’s respective top goalscorers Son Heung-min and Erling Haaland were absent while playmakers Maddison and De Bruyne had to be content with a place on the bench.

City’s notoriously poor record at Tottenham Hotspur Stadium was well documented and Guardiola’s side almost broke their duck in the fifth minute when Oscar Bobb tapped home on the goal line.

Bobb pounced after Vicario had denied Phil Foden from close range, but City youngster Bobb was adjudged by VAR to be marginally offside and it remained 0-0.

The visitors continued to seek a maiden goal at this venue and after Bernardo Silva and Mateo Kovacic had efforts blocked, Guardiola let out his first sign of exasperation when Josko Gvardiol sent a cross into the stand.

Spurs had barely had a kick but were given some unexpected respite when a three-minute delay to proceedings occurred due to one of Paul Tierney’s assistant referees having an issue with his technical equipment.

When play did get back under way, normal service resumed and a succession of last-ditch defending denied City in the 41st-minute with Bobb’s left-footed strike thwarted by Pedro Porro’s block.

Foden was the next to try his luck but fired wide from Bobb’s cut back to ensure it was goalless at the break.

Micky van de Ven made a vital intervention straight after half-time when Julian Alvarez had a sight of goal before Tottenham finally caused a moment of panic for the away side.

Timo Werner sent Brennan Johnson through on goal, but City’s back-up goalkeeper Stefan Ortega was out quick to dive at the feet of the forward.

It reenergised the home crowd although Guardiola turned to his ace in the pack with 65 minutes on the clock when De Bruyne was introduced.

Postecoglou followed suit eight minutes later and Maddison earned a hero’s reception on his return, but his first involvement was to bundle Silva to the floor in the penalty area.

Referee Tierney waved away appeals before Spurs and in particular Pierre-Emile Hojbjerg received two slices of luck.

A Hojbjerg air kick allowed Silva a chance but he fired straight at Vicario before Tottenham’s Danish midfielder gave away possession to Foden.

Foden teed up De Bruyne, who inexplicably curled wide from 16 yards and when Vicario saved from Jeremy Doku moments later, a replay was on the cards.

Ake had other ideas and when Vicario flapped at De Bruyne’s corner, the City defender was on hand to poke home and send the holders through to the last 16.

Ange Postecoglou has praised Tottenham vice-captain Cristian Romero for stepping up in Son Heung-min’s absence.

Spurs are without current skipper Son due to his international commitments with South Korea and Romero is set to wear the armband again in Friday’s FA Cup tie with Manchester City.

Romero was captain for the 2-2 draw at Manchester United two weeks ago and Postecoglou talked up his growing leadership qualities.

He said: “There’s definitely a void there but with all these things there’s definitely opportunities. That’s where Romero has really stepped up.

“You just feel it around the place. He knows that Sonny’s not here and he knows what Sonny does on a daily basis.

“Sonny gets around everyone in the building and says, ‘how you going?’ and Cristian’s doing that now. I can see that. In training he’s a lot more vocal than he was in the past. That’s the beauty of it.

“There is a void because you’re missing one of your leaders, but for me, on the outside, you’re kind of waiting on, ‘is anyone going to step up here because we’re going to need someone to or do I need to interject myself into it?’ But he’s stepped up.

“There’s been others too, Vic (Guglielmo Vicario) in goal, he’s stepped up.”

Postecoglou watched his team endure a horrid November period where they were hit with a string of absentees.

Spurs were able to regroup during December and while they remain without Son, Pape Sarr and Yves Bissouma due to the Asian Cup and Africa Cup of Nations respectively, the Australian feels the adversity has accelerated the growth of his young group in his debut campaign in charge.

“There’s a really good feeling amongst the group at the moment over where they’re at,” Postecoglou added.

“They understand that because of what we’ve been through, ‘OK, somebody’s missing, man down, but somebody fills that void and we keep going until they come back’. I think it’s been good for the growth of the team.

“This year for me is about growth. You don’t want to orchestrate these scenarios where we get challenged and have players missing, but the fact that we’ve gone through it, I just think has accelerated our growth.

“We could have flown through this first half of the year and I’m sure all the questions to me would’ve been, ‘what happens when there’s a hiccup?’ and I wouldn’t have been able to answer that question.

“I’d bluff my way through it but I wouldn’t have been able to really answer it.

“But I already know, I’ve seen the resilience and part of that is how I’ve dealt with those absences.”

Ange Postecoglou knows James Maddison is eager to make up for lost time but has admitted the Tottenham playmaker found his spell on the sidelines tough.

Maddison will return for Friday’s visit of Manchester City in the FA Cup after almost three months without football due to ankle ligament damage.

It halted Maddison’s brilliant start to life at Spurs and Postecoglou revealed the England midfielder struggled at times during the longest absence of his career.

“Not low but it was tough for him, because he does love his football, he loves the environment of football clubs, he loves the dressing room,” Postecoglou said.

“He’s kind of a force within that. It’s hard for all players when they’ve got to go through rehab, especially a character like him.

“I suggest that our sports science staff wouldn’t enjoy the one-on-one with Madders. He’s more of a guy who wants to be in the group.

“We did send him away in the middle of it. We felt it was good for him to get away with his family, we sent a physio with him (to Dubai).

“I think that helped bridge that time. When he got back from that, he was refreshed.

“Once he could see the finish line of ‘OK, I’m getting to the tail end of it,’ you could see his spirits lift. It’s been good to get him back.

“I know what Madders expects and, in training, you wouldn’t know that he’s missed so much. The quality is there straight away and everyone notices it and he’s looking good physically.

“And he’s the kind of guy who will want to make up for lost time and come back in and make an impact straight away.”

Spurs have not played for two weeks and the break has enabled Maddison to return to full fitness while Ben Davies and Dane Scarlett have recovered from hamstring problems.

Dejan Kulusevski is also available after illness ruled him out of the 2-2 draw at Manchester United a fortnight ago, but Giovani Lo Celso is still sidelined with a muscle issue.

Postecoglou gave his squad four days off during their mid-season break and, while plenty travelled far and wide to the likes of Dubai and Miami, the coach stayed at home to catch up with his family, who were in Australia for Christmas, and also put plans in place for the future.

He added: “My family were away and they just got back, so it was some quiet time at home.

“I kind of use those moments to look a bit farther down and see stuff that needs to do. While the cold face of it is games to prepare for and win, there is some longer-term stuff I am still keen to build within the club.

“You start mapping out those things and see if we can make an impact now or a bit later or when we are going to make an impact.

“It all helps you to get to where you want. Everybody wants to get away but even if I got away I would be thinking along those lines.

“I take what I do really seriously and I feel that sometimes if I switch off for too long, I am kind of missing something. That is the way I am wired.”

James Maddison is available for Tottenham’s FA Cup tie with Manchester City but boss Ange Postecoglou has yet to make a decision on whether he will start Friday’s clash.

Maddison has not played for Spurs since he sustained ankle ligament damage in a 4-1 defeat to Chelsea on November 6.

England international Maddison flourished after he moved to the club in a £40million deal from Leicester last June, scoring three goals and providing six assists in 12 appearances, and he will return to action against FA Cup holders Man City.

Postecoglou revealed: “He’s trained all week and he is fine.

“He is available and ready to start… when someone is available I assume they are ready to start.

“Whether they do or not depends on what I see with everyone else tomorrow and I usually make those decisions on game day.

“Like I said, the beauty of it is he’s got through the week really well and is ready to go.”

The billionaire former owner of Tottenham Hotspur, Joe Lewis, has pleaded guilty in an insider trading case in the US, prosecutors have confirmed.

Lewis, 86, pleaded guilty in front of US District Judge Jessica Clarke on Wednesday to charges alleging he had committed securities fraud and conspired to commit securities fraud by insider trading.

“Today’s guilty pleas once again confirm – as I said in announcing the charges against Joseph Lewis just six months ago – the law applies to everyone, no matter who you are or how much wealth you have,” said US Attorney Damian Williams.

“Billionaire Lewis abused inside information he gained through his access to corporate boardrooms to tip off his friends, employees and romantic interests.

“Now, he will pay the price with a federal conviction, the prospect of time in prison and the largest financial penalty for insider trading in a decade.”

Separately, Broad Bay Ltd, a company which is owned by Lewis, pleaded guilty and accepted its participation in hiding the billionaire’s stake in a pharmaceutical company. It will pay more than 50 million dollars (£39 million) in financial penalties.

Lewis’s lawyer David Zornow said that his client still has the right to appeal if he is sentenced to time in prison, according to Reuters.

The billionaire had in July denied the 16 charges of securities fraud and three charges of conspiracy that he was faced with. He will be sentenced on March 28.

According to prosecutors, he allegedly orchestrated “a brazen insider trading scheme” and passed secrets to romantic partners, personal assistants, friends and two co-conspirators.

The information allowed them to bet on companies which he had invested in, using information only those with access to the business could have known. It helped them earn millions of dollars, the case claimed.

Lewis built his wealth through the investment company, Tavistock Group, and bought a controlling stake in Tottenham Hotspur in 2001.

In 2022 he ceded control of the club and formally handed his stake to a family trust and has no day-to-day involvement with the club. Spurs declined to comment.

He was worth more than £5 billion according to the 2023 Sunday Times Rich List, being ranked as the 39th richest person in the country.

Clubs’ desire to avoid tough sanctions for financial rule breaches could be a big factor in the spectacular drop in Premier League transfer spending this month, a football finance expert has said.

Financial services firm Deloitte has told the PA news agency that by January 23 last year £435million had been spent by the 20 top-flight clubs – 10 times more than by the same date this year.

Spending reached a record £815m by the end of the January 2023 window, but so far this month Tottenham’s purchase of Romania defender Radu Dragusin from Genoa for a reported £26.7m is one of a small number of permanent deals to have been completed, with loan moves dominating.

The relative quiet comes following a 10-point deduction imposed on Everton in November by an independent commission for breaching the Premier League’s profitability and sustainability rules (PSR). The commission found the club had acted “irresponsibly” and concluded they “overspent”, largely on the purchase of new players.

Everton expect to learn the outcome of their appeal against that sanction by the end of next month, but were referred to an independent commission again earlier this month, along with Nottingham Forest this time, for breaching PSR in the period ending last season. Those cases should be resolved before the end of this season under a new fast-track process agreed by the clubs.

Tim Bridge, lead partner in Deloitte’s Sports Business Group, told PA: “It would be remiss not to talk about the impact (on transfer spending) of some of the regulatory moves that the Premier League has made and the independent bodies that work with the Premier League have made to really focus on how the Premier League is governed.

“You look at what’s happened with Everton, you look at what’s happened with Nottingham Forest, obviously there are ongoing investigations with other clubs as well.

“That will, I expect, have driven an underlying caution and also a real need to ensure that any value in the transfer market is as good as it possibly can be.”

Bridge did not rule out a “late flurry” of activity in the final week of the window but added: “I do think that some of those deals that maybe we’re used to seeing earlier in the window are either not being considered because of the regulatory challenge and the need to be compliant, which is a good thing, but also that element of the selling club really wanting to make sure that it drives the absolute value (of their players).”

Mauricio Pochettino endured a rocky start to life as Chelsea boss but has now guided the Blues to the Carabao Cup final as he looks to end his wait for a first trophy in English football.

The Argentinian has managed almost 400 games in England across spells with Southampton, Tottenham and now Chelsea but has yet to lift silverware in this country.

Here, the PA news agency looks at how Pochettino has fared in his quest for trophies.

Southampton

2013/14

Having taken over during the previous campaign with Saints already out of both domestic competitions, Pochettino’s early involvement in the League Cup and FA Cup was brought to a close by Sunderland. The Black Cats won 2-1 in a fourth-round League Cup tie at the Stadium of Light before claiming a 1-0 victory in the FA Cup fifth round.

Tottenham

2014/15

While a 2-1 fourth-round FA cup defeat at home to Leicester and a 3-1 aggregate loss to Fiorentina in the last 32 of the Europa League hardly set the pulses racing in Pochettino’s first season at Spurs, he did almost start life in north London with a trophy. Home wins over Nottingham Forest, Brighton and Newcastle took Tottenham into a League Cup semi-final against Sheffield United, with a 3-2 aggregate success setting up a Wembley final against Chelsea, who ran out 2-0 winners.

2015/16

Pochettino suffered from second-season syndrome in the cup competitions, losing 2-1 to neighbours Arsenal in the third round of the League Cup and slipping to a fifth-round exit in the FA Cup courtesy of a 1-0 loss to Crystal Palace. Achieving European qualification in his first campaign at the helm also led to little as Spurs were thrashed 5-1 on aggregate by Borussia Dortmund in the Europa League last 16.

2016/17

A 2-1 loss to Liverpool in the fourth round of the League Cup was forgivable, but, having ensured a return to Champions League football, Pochettino’s Spurs were knocked out in the group stage and then slumped to a 3-2 aggregate loss to Gent in the Europa League last 32. There was some comfort from an FA Cup run that included wins over Aston Villa, Wycombe, Fulham and Millwall before Chelsea ran out 4-2 victors in a semi-final clash at Wembley.

2017/18

There was another fourth-round League Cup exit – this time in a 3-2 loss to West Ham – but this season saw Spurs top their Champions League group before agonisingly losing 4-3 on aggregate to Juventus in the last 16. There was more Wembley misery in the FA Cup as Spurs reached the semi-final for a second successive season, only to lose 2-1 to Manchester United, having taken the lead through Dele Alli.

2018/19

A forgettable FA Cup campaign ended with a 2-0 loss to Crystal Palace in round four, but even a penalty shootout loss to Chelsea in the League Cup semi-final was not the heartbreaking moment of Pochettino’s final full season in charge. Having secured memorable late wins over Manchester City and Ajax to reach the Champions League final, Spurs were second best as an early Mohamed Salah penalty and a Divock Origi goal saw Liverpool win 2-0 in Madrid.

Chelsea

2023/24

Having won Ligue 1 and the Coupe de France at Paris St Germain, Pochettino returned to England when he was appointed Chelsea boss last summer. While results in the Premier League have been mixed, the 51-year-old saw his side beat AFC Wimbledon, Brighton, Blackburn and Newcastle in the Carabao Cup before recovering from a 1-0 loss at Middlesbrough in the semi-final first leg to thrash the Sky Bet Championship side 6-1 on Tuesday night and reach Wembley – where either Fulham or Liverpool await.