Middlesbrough marched into the second round of the Carabao Cup with a 3-2 victory at 10-man Huddersfield.

Kian Harratt gave the hosts an early lead but Jaheim Headley’s 13th-minute red card handed Boro the initiative.

And goals from Samuel Silvera, Isiah Jones and Riley McGree wrapped up victory for Michael Carrick’s visitors before Kyle Hudlin’s late consolation.

Huddersfield led inside four minutes a Harratt pounced on a Boro defensive error and fired home his first senior goal.

But Town’s hopes were hit when last man Headley bundled Isiah Jones over and was given his marching orders.

Carrick’s side drew level in the 20th minute when Silvera’s shot struck both posts on its way in.

After the break, Martin Payero came close to poking Boro in front after some uncertain Town defending.

And the visitors took the lead in the 63rd minute as an inspired threaded pass from Dan Barlaser found Jones, who flicked the ball past onrushing goalkeeper Chris Maxwell.

Substitute McGree added a third with eight minutes left when he cut on to his right foot and fired low past Maxwell.

Hudlin headed home in the fourth minute of added time but Boro held on to progress into the second round.

Chelsea are reportedly the subject of a Premier League investigation for alleged breaches of financial regulations during Roman Abramovich’s time at the club.

It has been reported current owners Todd Boehly and the Clearlake Capital Consortium, who took over last summer after Abramovich was forced to sell following sanctions as a result of Russia’s invasion of Ukraine, flagged the potential issue to the Premier League and Football Association themselves.

UEFA announced last month it had been approached “proactively” by the club, who agreed to pay 10million euros (£8.57million) to Europe’s governing body after owning up to “incomplete financial reporting” between 2012 and 2019.

Chelsea said in a statement at the time their new owners became aware of potential impropriety when carrying out a “thorough due diligence process” prior to the purchase.

According to reports, no charges have yet been brought by the Premier League but, even though the allegations relate to a previous ownership, possible sanctions could include a fine or points deduction if the club are found guilty of any wrongdoing.

The PA news agency has contacted Chelsea and the Premier League for comment.

A late dig was not enough for Neah Evans as she missed out on the medals to surrender her title in the women’s points race at the UCI Cycling World Championships in Glasgow.

Less than twenty-four hours after winning the Madison crown alongside Elinor Barker, Evans found she was missing the extra kick she needed in a race won by Belgium’s Lotte Kopecky ahead of Australia’s Georgia Baker.

Evans started strong and had followed an attack from Kopecky and Baker midway through the race, looking to gain a lap on the field.

But the pair opened up a small gap to Evans, and while they could work together to pick up the points, Evans had to chase alone, putting in an effort that would cost her later on as she later lost the lap she had worked so hard to gain.

Evans then tried to go long to get the points she needed in the final sprint but could not respond to an attack from Japan’s Tsuyaka Uchino.

“The race didn’t quite go as I was hoping, so I tried to adapt,” Evans said. “I just tried to reset and relax and I relaxed too much. I think I didn’t have the usual zip in my legs.

“I thought, ‘oh, crap. I cannot close that gap that I normally can close easily’. It just changes the dynamic. I went much earlier in the final sprint that I would normally but I didn’t feel like I had the zap to sprint.

“I will have to go for a long one and I couldn’t hold on it, which I normally can. A pretty frustrating day. It is what it is, it’s bike racing.”

Kopecky had not raced in Monday’s Madison after her usual racing partner in the event, Shari Bossuyt, returned a positive test for the banned substance Letrozole in March.

Evans came into these worlds, on her home track in Glasgow, still suffering the effects of a training crash last week, the injuries still visible on her right leg.

Although that did not stop her and Barker winning in the Madison, she could not back it up a day later.

“Up to the crash, I was having a brilliant lead-in,” the 33-year-old said. “I thought, ‘I am going to be fine’, but then you have that little step up. You say it is not going to affect you, it won’t make any difference, but you know it is going to.

“At this level just a few watts missing is the difference between being able to close the gap or not. So is what it is.”

Evans was not involved in this week’s women’s team pursuit, in which Great Britain took a first world title since 2014, with the fight for selection hotting up a year out from the Paris Olympics.

“The thing with being part of British Cycling is we have amazing support and amazing structure but it also means we have some incredible riders,” she said. “So it is hugely competitive to get a spot on the start line.

“I’d like to think I am in the mix, definitely after the Madison, but a lot can happen within a year.”

Andy Murray is through to the second round of the National Bank Open after beating Lorenzo Sonego in Toronto.

The 36-year-old, who has won the title in Canada three times – most recently in 2015 – battled past Italian Sonego 7-6 (3) 6-0.

In a marathon first set, Murray had to save two set points at 5-4 on his own serve.

The Scot dropped the first two points of the ensuing tie-break but won the next six to take control and wrap up the set in 88 minutes.

If that opening set was a slog, the second was a breeze by comparison.

The first break of serve in the match went to Murray and he quickly backed it up with two more.

He converted his first match point in typical fashion, grinding Sonego down in a punishing rally, to secure the victory in two hours and nine minutes.

The New Orleans Saints are beefing up their roster just days ahead of their preseason opener.

The Saints plan to sign running back Kareem Hunt and linebacker Anthony Barr, pending the former Pro Bowlers pass their physicals.

The news was first reported Tuesday by Dianna Russini of ESPN, one day after both veteran free agents visited the team.

Hunt spent the past four seasons with the Cleveland Browns and joins a Saints team looking to find a suitable replacement for Alvin Kamara after the five-time Pro Bowl running back was suspended for the season's first three games for violating the NFL's personal conduct policy.

Jamaal Williams and rookie Kendre Miller are also in the mix to get the start in New Orleans' season opener against the Tennessee Titans on September 10.

The 28-year-old Hunt played in all 17 games last season as Nick Chubb's backup, rushing for 468 yards and three touchdowns on 123 carries for an average of 3.8 yards per attempt.

A third-round draft pick by the Kansas City Chiefs in 2017, Hunt earned Pro Bowl honours and was named the 2017 Offensive Rookie of the Year, amassing career highs of 1,327 rushing yards and eight rushing touchdowns with 53 receptions for 455 receiving yards in his first year.

The 31-year-old Barr played in 14 games for the Dallas Cowboys in 2022, registering 58 total tackles and a sack, after spending his first eight pro seasons with the Minnesota Vikings.

A first-round pick by the Vikings in 2014, Barr has been selected to four Pro Bowls - most recently in 2018 - and is expected to help with linebacker depth after Andrew Dowell was lost for the season due to a torn ACL while Demario Davis is nursing a calf injury.

The Saints, who finished 7-10 last season to miss the playoffs for the second year in a row after winning four consecutive NFC South titles, play the Kansas City Chiefs on Sunday in their preseason opener.

Caroline Wozniacki made a winning return to the court at the National Bank Open in Montreal, more than three years after bidding farewell to tennis.

The 33-year-old, who walked away from the sport following the 2020 Australian Open and has since had two children, looked like she had never been away as she swept past Australian qualifier Kimberly Birrell 6-2 6-2.

“It feels great, my first match back in over three years and I was definitely a little rusty,” she said on court. “But what an amazing place to come back to play my first match.”

Wozniacki was understandably nervous at the start and threw in two double faults on her way to dropping serve in the first game.

But with the breezy conditions making serving tricky, five of the first six games were breaks, with Wozniacki’s sole hold giving her the advantage and she wrapped up the opening set in 43 minutes.

The former world number one, who won the Australian Open in 2018, aims to be fully up to speed in time for the US Open later this month.

So she will have been pleased with the battling service holds she had to make as the plucky Birrell put her under pressure in the second set.

However, Wozniacki finished the job on her first match point, a backhand winner down the line before raising her arms in delight.

However, it is straight back to parental duties for the Dane following her first win as a mother.

“That’s pretty crazy,” she added. “I was just looking at the clock and my kids are napping now. That’s the good part about playing early – I still have the afternoon with them.”

Arsenal have agreed a deal to sign Brentford goalkeeper David Raya.

The PA news agency understands a fee of £30million has been agreed for the 27-year-old Spaniard, who is reported to be signing a five-year contract.

Raya will provide competition for established number one Aaron Ramsdale and the England international welcomes it.

“Bring it on. Nothing comes easy in football. At the same time you need to move along and adapt as well,” Ramsdale told ITV Sport.

“I’ve done it to other people when I’ve moved clubs so I’m not going to be thinking that it’s never going to happen to me.

“If it happens, it happens and then we’ll fight and we’ll make each other the best version of ourselves because that’s what the manager is telling us as well.

“And I’m sure whoever plays, me or whoever comes in, the goalkeeping union – people laugh at it but it’s a real thing – (means) your individual disappointment will go away.

“You will put the team first and you’ll put that goalkeeper first as well.”

Raya’s arrival will also signal the departure of United States goalkeeper Matt Turner to Nottingham Forest in a deal which could be worth up to £10m.

Kevin Ryan is planning to saddle both Triple Time and Hi Royal in the Prix Jacques le Marois at Deauville on Sunday.

Triple Time has been kept fresh since causing a 33-1 upset in the curtain-raising Queen Anne Stakes at Royal Ascot and is firmly on course for a cross-Channel raid this weekend.

His younger stablemate Hi Royal was placed in both the 2000 Guineas at Newmarket and the Irish Guineas at the Curragh in the spring, but never threatened to land a blow in last month’s Prix Jean Prat.

However, he too is being readied for a return to Deauville, with William Buick booked for the ride.

Ryan said: “Both horses are in good form, Triple Time was very good at Royal Ascot and I’m looking forward to running him again.

“Hi Royal has always been a very consistent horse other than his last start and he’s been working well.

“Neil Callan will obviously ride Triple Time and William Buick has become available and rides Hi Royal.”

Conditions have been testing recently but a dry week both here and in France should see the ground improve and Ryan is hopeful the going will not be an issue at the weekend.

He said: “It’s a dry week, the ground today was good to soft and I don’t think there’s any rain forecast – it should be drying out all the time.”

Ireland back-rower Jack Conan remains an injury concern ahead of the Rugby World Cup after missing his country’s week-long training camp in Portugal.

Andy Farrell’s squad flew to the Algarve on Monday but Conan remained in Dublin to rehabilitate the foot problem he sustained in the first half of Saturday’s 33-17 victory over Italy.

Head coach Farrell talked down the severity of the issue in the immediate aftermath of the match but will not discover the full extent of it until next week.

Ireland host England at the Aviva Stadium a week on Saturday, with Farrell scheduled to announce his final 33-man squad for France on Monday, August 28 following a final warm-up fixture against Samoa.

Defence coach Simon Easterby said: “You would have seen after the game that there were a couple of players carrying bumps.

“The only person that hasn’t travelled with us from the squad is Jack Conan. He’s stayed behind just to rehab and we hope to get more information on his injury next week.

“We’re still waiting on assessment and we decided that it would probably be best for him to stay back in Dublin.”

Leinster player Conan was pictured with his right foot in a protective boot after departing the field just before half-time against the Azzurri.

The 31-year-old last week spoke of having unfinished business at the World Cup after his trip to Japan in 2019 was ruined by a stress fracture in his foot.

Full-back Jimmy O’Brien and scrum-half Craig Casey also sustained injuries at the weekend but have travelled with the rest of the squad.

Ireland are preparing to play an unofficial training match against Portugal on Wednesday, which should be beneficial for suspended captain Johnny Sexton.

The 38-year-old fly-half, who has not played since sustaining a groin injury at the end of the Six Nations, cannot return to competitive action until his country’s World Cup opener against Romania on September 9 due to a three-match ban.

Easterby insists the session “isn’t a full-blown game”.

“It wouldn’t be the first time it happened,” said Easterby. “Often teams collaborate with other teams and get the opportunity to do some set-piece against each other and to run some backline against backline.

“It certainly isn’t a full-blown game. It’s a condition training session which has been a collaboration between the Portuguese coaches and ourselves around trying to create a training session which is slightly different from the norm.

“When you know each other so well and get the opportunity to train against each other for four or five weeks, you often cancel each other out in terms of what you try and do in attack and defence.

“I guess it’s one of those opportunities we had to connect up with the Portuguese to train against them and to challenge ourselves in way you wouldn’t normally do in a normal training week.

“He (Sexton) will be playing a part in the training session, for sure – as will every other player that’s here.”

Manu Tuilagi and Ollie Lawrence could be paired together in a potent centre combination as England assess their midfield permutations for the World Cup.

Head coach Steve Borthwick believes that despite broad similarities in playing style – both players are physical carriers who run through rather than around opponents – they can forge an effective partnership.

It raises the prospect of England entering the crucial opener against Argentina on September 9 with Tuilagi and Lawrence operating outside fly-half Owen Farrell.

Lawrence entered the World Cup training camp on the back of his breakthrough Six Nations, filling the hard-running role usually performed by Tuilagi.

“I think they can play together – Manu at 12 and Ollie at 13,” Borthwick said.

“That was Ollie’s first proper Six Nations, as in being involved every week. He did really well before unfortunately having to go off in the France game with a hamstring injury.

“Ollie brings carry but he’s also a very good defender. He rates exceptionally high as a defender on all the systems we use to analyse performances across the Premiership.

“We know Manu’s strengths and experience and I think they can play together in a specific way.”

Other centre options in the 33-man World Cup squad named by Borthwick on Monday are Joe Marchant and Elliot Daily, both of whom are comfortable in the number 13 jersey.

Farrell can play at inside centre with George Ford and Marcus Smith present as additional fly-halves.

Borthwick on Thursday picks his team to face Wales at Twickenham in the second instalment of the double-header between the old rivals.

Having crashed to a tame defeat in Cardiff last Saturday, England are already in must-win territory with the Summer Nations Series reaching the midway stage this weekend.

Wing Jonny May, centre Guy Porter and lock Jonny Hill – each of whom was omitted from the World Cup squad – have been retained as injury cover ahead of the team announcement.

Frankie Dettori is keen for the equine stars to be the focus of attention on Qipco Champions Day, despite the fact the Ascot extravaganza will also be his swansong on European soil.

The entries for the five main races on the October 21 card were published on Tuesday, with the brilliant Paddington headlining a stellar cast

Having secured his fourth Group One victory of the season in the Sussex Stakes at Goodwood last week, Aidan O’Brien’s three-year-old has been entered for the both the £1.3million Qipco Champion Stakes and the £1.1million Queen Elizabeth II Stakes.

The three remaining Pattern races – the Long Distance Cup, the British Champions Sprint and the Fillies & Mares Stakes – each offer a total prize fund of £500,000, meaning prize money for Champions Day totals £4.1million, cementing its position as the richest raceday in the British calendar.

Entries also include the unbeaten Prix du Jockey Club winner Ace Impact and the last two Betfred Derby winners in Auguste Rodin and Desert Crown, as well as other Group One stars in the shape of the impressive Prince of Wales’s winner Mostahdaf and star sprinter Shaquille, winner of both the Commonwealth Cup and the July Cup this season.

But for all the brilliant action set to take place on the track, for many the star attraction will be Dettori, who is set to make his final appearance in Britain and Europe before retiring from the saddle later in the year.

He said: “Qipco British Champions Day is a great concept with great prize money. Racing for the kind of money which the rest of the world is doing more regularly.

“It was very hard to pick my last day riding in England. I had thought about Newmarket the week before but Ascot is my favourite track with so many great memories. It is going to be a special day and my family is going to be there.

“I don’t want to take the gloss off the day. The day is about the best day’s racing and not about my last day riding here before I go to America for the Breeders’ Cup and then Australia and Hong Kong before retiring at the end of the year.”

Reflecting on some of his Champions Day highlights, the 52-year-old added: “It was very good last year with Emily Upjohn coming back to win (the Fillies & Mares) after a long layoff and then Kinross, my favourite horse, winning first the Prix de la Foret at Longchamp and then 13 days later the British Champions Sprint.

“Another highlight was Cracksman, who gave me a first win after years of trying in the Champion Stakes in 2017 and won it again the next year.”

New Liverpool captain Virgil van Dijk understands why some sections of the fanbase are heading into the season apprehensive about what it may bring but he does not share their concerns.

There is growing unease over the club’s failure to recruit a defensive midfielder following the sale of Fabinho to Al-Ittihad and manager Jurgen Klopp has admitted he will have to find a quick fix from within the squad for this weekend’s opener at Chelsea.

After the departures of Jordan Henderson, also to Saudi Arabia, James Milner, Naby Keita and Alex Oxlade-Chamberlain there is little left of the core midfield which helped win the Champions League and Premier League in recent years.

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It means forward Cody Gakpo could be asked to drop back while £35million summer signing Alexis Mac Allister is likely to be deployed in the deep-lying role – which does not play to the Argentinian World Cup winner’s strengths – with fellow new arrival Dominik Szobozslai expected to make his Premier League debut.

The club’s stuttering pursuit of Southampton’s Romeo Lavia, who could fill the Fabinho role despite being only 19 and having made just 29 appearances in one top-flight season, has led to criticism from the likes of former Reds defender Jamie Carragher.

But as Van Dijk embarks on his maiden campaign as captain, having inherited the armband from Henderson, he remains confident they can find the improvements necessary to get back into the top four and challenge Manchester City and Arsenal.

“I can definitely understand it (fans’ negativity) in some ways but I’m not a very negative person, so obviously it’s not in my mind to think like that,” he said.

“But obviously when a lot of players are leaving, when your captain is leaving, your vice-captain is leaving, and at the moment there are only two incomings…

“And the way we have been playing, in possession really good but defensively when you concede goals it’s not as good I can understand some people having doubts.

“Let’s see if more players are coming in and then we have to be ready again for a long season. It will be very tough if we look at the teams around us, but we want to be up there again, we want to be challenging again.”

The loss of the majority of their midfield has not only left Liverpool short on numbers but also on experience, with 1,318 appearances in the middle of the park disappearing over the summer.

While Mac Allister, 24, has made 98 Premier League appearances for Brighton, the 22-year-old Szobozslai has just 62 Bundesliga games to his name in two seasons with RB Leipzig, although his consistently high numbers were one of the reasons Liverpool made their move.

Other realistic midfield options currently available are Thiago Alcantara and Stefan Bajcetic, who have not featured in pre-season as they continue to recover from injuries sustained last season. There is the 24-year-old Gakpo, with 21 league appearances in four months after joining in January, and academy graduate Curtis Jones, aged 22 with 63 league outings.

Van Dijk sees the loss of senior players as an opportunity for others to take up the mantle.

“We have to be confident, we should be confident and we should still be learning each and every day,” he added.

“There have been characters leaving, players who have played a big part in the success, but others have to step up.

“That’s a nice challenge in my opinion. We should be excited. I’m very excited, so let’s give it a go.”

Van Dijk himself is typically relaxed about his promotion to captain but knows he is following on from the ultra-successful Henderson, who lifted the Champions League, Premier League, FA Cup, League Cup and Club World Cup.

“Obviously we won everything together, and I was very sad to see him leave to be honest but that’s football, that’s life, and he has the right to do that in this case,” said the Dutchman.

“He made that decision but if I can be as successful as he was as a captain then I would sign (up) for that immediately.

“It’s step by step. I’m looking for consistency from our side, winning games, winning them the hard way at times, finding a way and creating a positive atmosphere where we all do it together.

“That’s how I want to attack the season and give everyone the assurance that we give everything for one another. Hopefully we will be successful.”

Bucanero Fuerte is set to renew rivalry with his Royal Ascot conqueror River Tiber in the Keeneland Phoenix Stakes at the Curragh on Saturday.

Aidan O’Brien claimed the Group One contest for a remarkable 17th time with Little Big Bear 12 months ago and is responsible for six of the 12 juveniles still in contention for this year’s renewal.

The Ballydoyle handler’s chief hope is River Tiber, who stretched his unbeaten record to three in the Coventry Stakes at the Royal meeting in June and is second only to stablemate City Of Troy in the ante-post betting for next year’s 2000 Guineas.

Alabama, His Majesty, Johannes Brahms, The Caribbean and Unquestionable complete the O’Brien sextet.

Just a length behind River Tiber when third in the Coventry was the Adrian Murray-trained Bucanero Fuerte, who subsequently proved that performance was no fluke by edging out Unquestionable in the Group Two Railway Stakes over the Phoenix course and distance.

Murray has also left his 150-1 Norfolk Stakes winner Valiant Force and Launch in the Group One contest at the six-day stage, but looks set to rely upon his Railway winner.

He said: “Bucanero Fuerte is the one that’s probably going to go.

“All has gone well since the Railway. We took him and Valiant Force to work at the Curragh last week and we were very happy with the two of them. Hopefully it’s onwards and upwards.

“You don’t know until you run, but looks like he (Bucanero Fuerte) is improving all the time.”

Assuming Bucanero Fuerte does line up at the Curragh, his stablemate Valiant Force could head to France in search of a Group One win of his own.

“He’s going to Deauville in two weeks’ time for the Prix Morny. We’re looking forward to it – the pressure is on,” Murray added.

The potential Phoenix field is completed by Donnacha O’Brien’s Porta Fortuna, winner of the Albany Stakes at the Royal meeting, Jessica Harrington’s Coventry fourth Givemethebeatboys and the Diego Dias-trained Gaenari.