Pep Guardiola does not expect Erling Haaland to be fit for Manchester City’s Premier League match against Crystal Palace on Saturday, and admitted the Norway striker is a doubt for next week’s Club World Cup fixtures.

City’s top scorer, who has 19 goals this season, missed last weekend’s win at Luton and the midweek victory over Red Star Belgrade with a foot injury, and has been receiving treatment in Marbella.

Haaland reported back at City on Friday morning and Guardiola said he would be assessed by club doctors before any further decisions are made.

City are due to travel to Saudi Arabia after Saturday’s match for the Club World Cup, with a semi-final against opponents yet to be determined on Tuesday. Either the final or the third-place play-off will follow on Friday.

“Haaland arrived today and the doctors will see him and we will see how he feels,” Guardiola said.

“He had treatment away. Hopefully he can travel to Saudi and we will see if he is able to play in the first game or the second game, or when we come back. I don’t think he will play [against Palace] but maybe he surprises me.

“It is not a fracture, just stress. Sometimes players recover quickly, some longer. Day by day, week by week, we see how he feels. The moment he doesn’t have pain he will play.”

City’s come-from-behind win at Kenilworth Road last Sunday ended a run of four league games without a win, and any talk of a mini-crisis of form has disappeared in the last week, with a young side earning a 3-2 win in Serbia with the help of goals from debutant Micah Hamilton and 20-year-old Oscar Bobb.

Both players are already older than the more established Rico Lewis, part of last season’s treble-winning squad, pointing to more encouraging work being done by the club’s academy, which besides first-team players has also contributed to the balance sheet with several youngsters sold on.

“For all the big clubs, the academy is an important part of many things,” Guardiola said. “We just see what happened in the last five or six years with academy players. They help us or they make a career away with a good transfer for the club to be sustainable economically.

“I know how important it is for our fans, our people to identify the young lads like Rico, Phil (Foden), Micah as well. Coming from being seven, eight, nine years old and being in the first team is something phenomenal.

“We continue to work on that and hopefully in future we can have more players like this.”

Palace will head to Manchester without a win in their last five Premier League matches, four of them defeats, but they enjoyed a famous win at the Etihad in October 2021 and have proven stubborn opponents on many occasions.

“It has always been a tough game,” Guardiola said. “How they defend is brilliant and they don’t need much at set-pieces with (Joachim) Anderson and the other guys. I don’t remember easy games against Roy Hodgson teams. With Patrick (Vieira) also, but especially with Roy.”

Asked if he could imagine still being in the game at Hodgson’s age, 76, Guardiola laughed.

“I don’t think so, but you never know!” he said. “To have the fire and passion inside to still be there and the team is really good.

“They played incredibly well against Liverpool, unfortunately they had a player sent off and with 10 against 11 against Liverpool it is almost impossible, but 11 against 11 I don’t know what would have happened.”

Xavi insists he does not feel “alone” despite the pressure building on the Barcelona coach.

The Blaugrana have suffered back-to-back defeats heading into Saturday evening’s encounter with Valencia.

Xavi’s men sit fourth in the table having been beaten 4-2 at home by La Liga leaders Girona last Sunday, leading to speculation around the former playmaker’s long-term future at Camp Nou.

However, Xavi is confident he has the backing of the club’s leadership and rated the fans’ support for his team as a “perfect 10”.

“I never feel alone. I feel like I have support and strength and I feel that we can have a great season,” he said at his pre-match press conference in quotes reported by the club’s X account.

“The fans are behind the team, they are a perfect 10. They know that we will give everything.

“We have a fantastic relationship, with the president (Joan Laporta), with (sporting director) Deco, with (vice-president) Rafa Yuste… I believe more than ever in the project and in what we are doing.

“The club needs stability. We are a winning project. We are the defending La Liga and Super Cup champions.”

Barca had bounced back from home defeat in the ‘Clasico’ against Real Madrid with three wins and a draw from their next four league games before the Girona setback.

A team showing seven changes then also lost 3-2 away to Royal Antwerp on Wednesday night in the Champions League, but with qualification for the last 16 already assured.

Barca go into the match at the Mestalla seven points adrift of Girona, five behind Real and below Atletico Madrid on goal difference.

They remain without long-term injury victim Gavi, who is out with a cruciate ligament tear. Goalkeeper Marc-Andre ter Stegen and defender Marcos Alonso, who are both suffering with back injuries, remain out of the squad heading into this weekend.

Valencia have not won any of their last four matches in La Liga, losing three and drawing one, but their striker Fran Perez was in bullish mood ahead of Barca’s visit to the Mestalla.

“We are working hard to hurt Barca and it’s going very well. We’re really looking forward to it,” he told the club’s in-house radio station.

“If we beat Atleti at home 3-0, why can’t we beat Barca at Mestalla? It’s going to be a very competitive game. The game is all about keeping a clean sheet and making the most of the chances we get. We can’t get distracted in any action.

“At Mestalla we are a very difficult team to beat. We have to be calm and compete well and I’m convinced that we’ll have a very good game.

“Our fans are very important and they are our 12th man. We are going to have a great game not only for us, but also for the fans, who deserve it.

“The tickets being practically sold out shows how the fans support us and we must respond with the highest possible level of demand. We must give everything for the club and for our fans.”

Valencia are 11th going into the weekend, with five wins, four draws and seven defeats from their 16 matches so far.

Liverpool manager Jurgen Klopp has paid little attention to Manchester United’s current troubles and believes the fact his side were one of the first to expose their weaknesses is of little relevance ahead of Sunday’s encounter.

Erik ten Hag’s side were humiliated 7-0 at Anfield by their arch-rivals in March in the largest defeat for either side in the clubs’ 211-match history as United crumbled in conceding three times in a seven-minute spell either side of half-time, shipping a further four in 22 minutes late on as the hosts ran riot.

Those deficiencies have been exploited by a number of other teams this season, though not quite to the same extent, with United having lost half of their 24 matches in all competitions to ramp up the pressure on Ten Hag.

But Klopp still remains wary of the old enemy, saying: “I never like when the headlines about United are not great before we play because it’s like ‘OK, then it is the game where they can put everything right’.

“The more bad things people say about them, the stronger they will show up. That is always the case. I don’t like that.

“I don’t follow United closely enough to know exactly what the problem is there but I saw Erik ten Hag was manager of the month last month and saw they were the team in form in the last month so how can it be all wrong? I just don’t understand it.

“The situation with Man United – and don’t get me wrong – it’s just not important for us as we just prepare for our team.

“I try to understand the situation of the opponent before a game, I really do, because I think it is important to know why they are motivated and want to put things right and sometimes I tell the players (his opinions) and sometimes I don’t tell the players.”

Before their humbling at Anfield last season, United were making a late charge to join the title race with eight wins and just one defeat in an 11-match run.

Ten Hag’s sixth-placed side are already 10 points behind Liverpool, the current leaders, and an eighth Premier League defeat of the campaign would almost certainly end already distant hopes of reeling in their rivals.

But Klopp insists inflicting more pain on their long-time adversaries is not a motivating factor.

“No. I have to think if I ever did that… I would probably say no. There is one thing we go for and that’s three points on a match day,” he added.

“If something helps for motivation? If it would be round about four matchdays before the end of the season and with that we could make the last step I would probably mention it but in this situation that’s just not important.

“The 7-0 we knew that day it was a freak result that happens once in a lifetime. If it helps anyone for the next game it is the team who lost 7-0 and not the team who won 7-0.

“If you take it all out of consideration and just play a football game against the historical rival of Liverpool at home at Anfield that itself must make it a special game and that’s what I want to see from us, a special game.

“It is a home game. It is for the people. We know what it means. No-one would expect us not to care. We care a lot (but) we cannot go nuts before the game already.”

Klopp’s main selection decision is around who to pair with Virgil van Dijk at centre-back with Ibrahima Konate and Joe Gomez having a half each alongside impressive 20-year-old Jarell Quansah in the 2-1 Europa League defeat to Union Saint Gilloise.

Ange Postecoglou has written a list and checked it twice, but is still patiently waiting to discover if Father Christmas has deemed his work naughty or nice this year.

While all Tottenham and Celtic supporters’ would put the Australian in the latter category for 2023, the fanbases of Arsenal or Rangers may have differing opinions.

Yet regardless of what side of the list Postecoglou ends up on, he knows his wish for Christmas will be difficult to achieve.

With eight players already out injured and Pape Sarr, Yves Bissouma and captain Son Heung-min set to be absent for at least some of January due to international commitments, the Spurs boss would dearly love to get new signings through the door at the beginning of next month.

“I wrote my letter to Santa. Like my kids, now I’ve just got to see whether I’ve been naughty or nice and see what I get mate,” Postecoglou joked when asked about progress on additions ahead of Friday’s trip to Nottingham Forest.

In a more serious tone, he continued: “Obviously with where we’re at injury-wise, the players we’re going to miss, we’ve got some significant games in January and signing somebody late in January could mean they haven’t been able to make an impact in those other games.

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“We’re pushing hard but you need all parties to agree to that.

“Other clubs, particularly if it’s players they want, will be wanting to hold on them for as long as possible for their own reasons through January.

“It is a challenge, I get that, but everyone at the club is working hard to get the best outcomes for us and we’ll see how it goes.”

Spurs boss Postecoglou has made clear his desire to sign a new centre-back in January and a versatile attacking player is also top of the club’s wishlist.

Eddie Howe will look back on his first Champions League campaign and agonise over the “if only” moments which cost Newcastle a place in the last 16.

The 46-year-old head coach steered the Magpies to within touching distance of the knockout stage only for their qualification hopes to be dashed by Wednesday night’s 2-1 home defeat by AC Milan, during which they were in pole position to progress when they led 1-0.

Instead of looking forward to the draw for the next round, Howe is instead preparing his injury-hit squad for Saturday’s Premier League clash against Fulham, with the controversial penalty decision which cost them victory at Paris St Germain and their failure to deal with the set-piece which led to Milan’s equaliser prominent in his thoughts.

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He said: “We were so close, so, so close while being really stretched with our resources, and that’s why I have to compliment the players on what they’ve given.

“It could have been very different and I just think we should take confidence from the fact that the hardest group, we were so close to achieving it.”

Newcastle secured a Champions League berth for the first time in 20 years courtesy of their fourth-place finish last season, an achievement which arrived barely 18 months into the tenure of their Saudi-backed owners and significantly ahead of schedule.

Asked if he had spoken to the ownership group and what had been said in the wake of Wednesday night’s disappointment, Howe replied: “ I think they see the work that goes on behind closed doors and they have close relationships with the players. We are like a family, we’re very close.

“That’s not just me with them, it’s everybody connected with the club. There’s just that feeling that they’re very supportive of the players and understanding of how much they’ve given. They can see the efforts on the pitch, and I think that’s the most important thing.

“That’s why I have no regrets over what the players have given over this Champions League campaign. I might have regrets over a couple of other things, but not at all over what the players have given. That’s always the biggest judgement for me.

“If you’re looking at it analytically, the players did incredibly well last year to finish where they did. It was miles ahead of schedule because, in pre-season, no one was talking about top four or Champions League football.

“You have to give the players a lot of credit, so what you can’t then do is give them a lot of credit and then hammer them at the same time because we couldn’t then follow that up.”

Howe did, however, admit that the exit from Europe could have financial implications for his January transfer budget.

He said: “Of course, going out of Europe will have repercussions financially for us because we’re going to lose revenue on games that we could have had, but that’s all been budgeted for and we’ll see where we stand.”

Influential full-back Kieran Trippier will miss Saturday’s game through suspension, while midfielder Joe Willock and striker Harvey Barnes, who has suffered a setback in his recovery from a toe injury, are unlikely to figure before the turn of the year.

Rebecca Welch’s historic appointment to officiate a Premier League match has been welcomed by Newcastle boss Eddie Howe.

The 40-year-old Welch will become the first female referee in top-flight history when she takes charge of the Fulham v Burnley match on December 23.

Welch was also fourth official for the Cottagers’ home game against Manchester United last month.

Howe applauded the decision to appoint Welch and said: “I think it’s a great moment.

“For me, it’s got to be based on ability, not gender, ability to referee and I fully support it.”

Sam Allison will become the first black man to referee a top-flight match in 15 years when he takes charge of the Sheffield United v Luton game on Boxing Day.

Kick It Out also welcomed the news of Welch and Allison’s appointments.

“Referees up and down the land are waking up this morning and thinking there are no barriers to get to the top,” the anti-discrimination charity posted on X.

“Visibility matters. Well done to @FA_PGMOL and organisations like @BAMERef for helping to create those journeys. There are many more inspirational stories to be told.”

England captain Harry Kane has enlisted the help of Google’s AI tool Bard to help his family get ready to settle into their new life in Munich.

Kane left boyhood club Tottenham in August to join Bayern Munich in a £100million transfer and has already scored 22 goals in 20 appearances for the German outfit.

While Kane has hit the ground running with Bayern, he has been living in Munich on his own after his wife Kate gave birth to their fourth child Henry a week after his big-money move.

However, Kane’s family are set to permanently join him in Germany shortly and the 30-year-old has joined forces with Google to showcase how Bard can help with every day situations on and off the pitch.

“I am excited to be teaming up with Google, especially on a product as impressive as Bard,” Kane said.

“I recognise how the potential of AI can help me in all sorts of ways with my move to Germany and to get my kids settled into a new life in Munich.

“Bard even suggested some new goal celebrations – we’ll have to see if I use them on the pitch!”

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During a series of short video clips, Kane asked Bard to help his children adjust to life in Munich by coming up with a bedtime story to explain why they should be excited about moving to Germany.

He also used Google’s AI tool to plan a treasure hunt through Munich’s most famous sights and got Bard to translate his most commonly used English phrases in post-match interviews to German.

Google UKI’s Eileen Mannion added: “We’re thrilled to be teaming up with Harry Kane on our latest campaign, which shows how Google’s conversational AI Bard can help anyone, even the England’s football captain, in everyday situations.”

What the papers say

The potential ins and outs at Manchester United continue to keep the rumour mill turning with Brazil midfielder Casemiro at the heart of the speculation. According to The Sun, via French outlet Sports Zone, Paris St Germain are keen on the 31-year-old with Saudi Arabian side Al-Hilal also interested.

There appears less interest among clubs in ending Jadon Sancho’s time at Old Trafford. The Sun says Manchester United are finding it hard to find a buyer willing to match the 23-year-old’s wages.

One former United player has teased a potential playing return on social media after leaving in the summer. The Daily Mirror reports David De Gea, 33, posted an Instagram message saying “Work, work, work” having been linked with Newcastle or even a shock return to Old Trafford.

Defender Tosin Adarabioyo’s return from injury at Fulham is attracting potential suitors. The Daily Mail says the 26-year-old is catching the eye having almost left for Monaco or Tottenham in the summer.

Social media round-upPlayers to watch

Cedric Soares: Arsenal’s Portuguese defender, 32, is catching the of Villarreal, says ESPN.

Kendry Paez: The 16-year-old Ecuador midfielder has trained with Chelsea according to The Daily Telegraph, having signed from Independiente del Valle in the summer ahead of a move on his 18th birthday.

Celtic completed the signing of Roy Keane on a free transfer on this day in 2005.

A month earlier, Keane had abruptly left Manchester United by mutual consent after his relationship with manager Sir Alex Ferguson deteriorated during a spell on the sidelines through injury.

Keane had been hurt in a challenge with Liverpool’s Luis Garcia in September of that year and grew frustrated while out.

He had already clashed with Ferguson during the club’s pre-season training camp in Portugal, and then angered the manager with an MUTV interview in which he said he was open to finishing his career elsewhere as his contract ran down.

A further MUTV appearance in early November did even more damage as the United skipper gave a damning assessment of some of his team-mates’ performances in a 4-1 defeat to Middlesbrough.

In 12 full seasons with United, Keane had won seven Premier League titles, four FA Cups and the Champions League, but Ferguson was his usual ruthless self and, as tensions mounted, he cut ties as Keane’s contract was cancelled.

Gordon Strachan’s Celtic pounced as Keane joined the club he had supported as a boy – the midfielder signing an 18-month deal.

He would have to wait until January to make his debut, but it came in a shock 2-1 defeat to First Division Clyde in the Scottish Cup.

A month later, Keane scored in a Scottish Premier League win over Falkirk, which proved to be his only goal for the club.

After helping Celtic to win both the league title and Scottish League Cup, Keane retired that summer on medical advice.

The announcement came a month after he had returned to Old Trafford for his United testimonial, a friendly against Celtic in which Keane played 45 minutes for each side.

Rangers manager Philippe Clement backed his side to have an “amazing season” if they show the same togetherness that helped them to a 3-2 win over Real Betis in Seville.

Kemar Roofe’s 78th-minute winner sent an under-strength Rangers into the last 16 of the Europa League.

The Light Blues twice took the lead in the first half through Abdallah Sima and Cyriel Dessers but they were heading for the Conference League knockout stages before Roofe’s late goal inflicted a first home defeat of the season on Real Betis.

Clement told Rangers TV: “It’s an amazing evening. I am really proud of the boys, they way they stuck together, the way they were brave. The things I asked – to be brave, to go with our football, create chances, score good goals, and a real top team mentality.

“That’s what we need to build on over the next couple of months.  If they stick together like this every three days, you always have an amazing season.”

It was Rangers’ first away victory against Spanish opposition.

Clement said: “This is a big reference and statement also, for them and the outside, that if everyone is into the story and working hard, we are a really hard team to beat, even for top-class teams like Betis, who are in really good form and played a really good game against Real Madrid last week and could have won.

“It was the first loss in their home stadium this season. And it was also a game we had to win, a lot of pressure and the players dealt really well with it.”

The Belgian remains unbeaten in 13 games as Rangers manager and can lift his first piece of silverware in Scotland when his side take on Aberdeen in the Viaplay Cup final this weekend.

“It was a really important evening and a moment to enjoy but not for too long,” he said. “We have a really big game on Sunday.

“I am also happy for all the fans who were here because the support was incredible, during the game, after the game. So I hope they put Hampden Park on fire, but not on fire with pyro, just with songs and the noise.”

Roberto De Zerbi hailed Brighton’s last-gasp 1-0 victory over Marseille to top Europa League Group B as a “historic moment” in the club’s history.

Joao Pedro smashed in an 89th-minute winner at the Amex Stadium to make sure the Seagulls avoided the play-off round and instead slotted straight into the last 16.

Italian De Zerbi, who masterminded progressing from a group that included Ajax and AEK Athens along with the French 1993 European Cup winners, said: “We haven’t won anything…yet, but we are really happy and proud.

“I told the players before the game that the game was more important for us than them. Marseille are used to playing in European competitions.

“To finish at the top of the table is a historical moment.

“The atmosphere during the game was incredible. The crowd were a 12th player like I’ve never seen before.

“It is important because we don’t have to play an extra game.

“After going 2-0 down in Marseille in the first game, we changed everything and after that game we won four games in a row with four clean sheets in a row. That is incredible.”

De Zerbi dedicated the result to the players and fans of former club Foggia – who lost a Serie C title decider to Gennaro Gattuso-managed Pisa in 2016.

His revenge on the now Marseille boss came courtesy of Joao Pedro – who ended the group stage with six goals and the competition’s leading scorer.

The Brazilian was threaded through by Pascal Gross before skipping past a tackle and thumping into the top corner, making the Amex erupt and De Zerbi jump into the crowd.

De Zerbi said of his goalscorer: “Joao is playing very well. He is becoming a great player in mentality – which playing for his national team has helped.

“The qualities of Joao are clear. We want to help him become a great player.”

Joao Pedro added: “I’m very happy. These are the best moments of my life. Thank you to my team-mates, they always support me.

“I’m very happy to be top scorer in the Europa League. To be top of the table, in the league or top scorer, you need to keep going through hard work.”

Marseille just needed a draw to avoid a play-off match against one of the teams that finished third in the Champions League.

Jonathan Clauss and Amine Harit both hit the woodwork before the visitors parked the bus, only to be undone by Brighton’s late winner.

Boss Gattuso said: “We knew what type of match this would be. We knew what level Brighton play at and the quality they have.

“We prepared to face them but their level of quality was too strong.

“We didn’t lack courage but it is the quality in the end that showed.”

David Moyes hailed Edson Alvarez’s performance after the Mexican starred in West Ham’s 2-0 victory over Freiburg to book their place in the last-16 of the Europa League.

Alvarez produced a wonderful assist for Mohammed Kudus in the 14th minute before the midfielder turned scorer later on.

And Moyes lauded both Alvarez and Kudus who were signed from Ajax in the summer.

“He did great (Alvarez),” Moyes said.

“The assist for the first one was a great pass then he did a great bit of link up with Jarrod (Bowen) and scores a big goal so I’m really pleased for him tonight.

“He’s still recovering a bit with illness but I’m really pleased with the things he’s done.

“The two of them (Kudus and Alvarez) have made great contributions already.

“Mainly Mohammed with goals and Edson with other elements and the two will get better.

“The hardest bit to find is the consistency with the intensity of the games.

“They’ve both settled in really well and they’ve done a good job.”

West Ham will avoid playing in the last-32 after tonight’s victory.

Moyes admitted the victory which sealed West Ham’s place at the top of Group A will give his side respite in February.

The Scot also highlighted the Hammers’ emergence in Europe in the last three years.

He added: “It is hugely important for us to get a bit of breathing space in February which we wouldn’t of had if we finished second.

“Qualifying for Europe and winning the group three years in a row now is really good for a side who has not been regular attendees.

“I think that’s 10 wins in Europe in a row now and that’s good for any team. Our control was pretty good and we’ve learnt from the games.

“Tonight we deserved our victory and deserved to top the toughest group out of the three previous years.”

Freiburg manager Christian Streich highlighted West Ham’s quality on the night.

He said: “It’s difficult to shut the gaps down. Jordy Makengo was playing against a top player like Kudus.

“Lucas Paqueta has got fantastic quality and I could really mention the whole team.

“If you don’t play at the highest level it is hard to play against the team at the level of West Ham.”

Former MKE Ankaragucu president Faruk Koca has been handed a permanent ban by the Turkish Football Federation for punching referee Halil Umut Meler.

Meler was approached and hit in the face by Koca following Monday night’s Super Lig match between Ankaragucu and Caykur Rizespor.

Koca was subsequently arrested and the TFF, in announcing a host of disciplinary measures on its official website on Thursday night, said the 59-year-old has been banned in response to the incident, which has made headlines across the world.

Meler had sent off one player from each side before Rizespor equalised in the seventh minute of injury time to force a 1-1 draw, with Koca running onto the pitch after the game before hitting the referee, who was then kicked by another person while on the ground.

Meler left hospital on Wednesday after being treated for injuries, including a small fracture under his eye.

The country’s justice minister, Yilmaz Tunc, said on his X account on Tuesday that Koca had been arrested “for injuring and threatening a public servant due to his public duty”. Koca later announced his resignation as president via the Ankaragucu website.

Matches across all of Turkey’s leagues were suspended following the assault and it has since been confirmed by the TFF – which has also fined Ankaragucu £54,000 and ordered them to play five games behind closed doors among a number of sanctions following the incident – that they will resume next Tuesday.

FIFA president Gianni Infantino condemned the attack on Thursday, telling Sky Sports News: “Enough is enough and this has to stop. I was shocked when I saw the images like everyone else.

“You can be excited at a match and you can feel for a team but there is no way we can accept anything like that to happen.”

West Ham qualified directly for the last 16 of the Europe League after a convincing 2-0 win over Freiburg at London Stadium saw them finish top of Group A.

Mohammed Kudus opened the scoring in 14th minute before Edson Alvarez’s strike just before half-time confirmed victory for the Hammers, who had started the match level on 12 points with their German opponents in the race for top spot.

David Moyes’ men bounced back after last weekend’s 5-0 Premier League mauling at Fulham to earn a seeded position in the knockout stages and avoid a play-off.

The hosts, chasing a 10th successive home win in Europe, came close to taking an early lead when Lucas Paqueta struck the Freiburg crossbar in the fifth minute.

A drop of the shoulder by Kudus saw the tricky attacker beat his man before delivering a cross to Paqueta who thundered his effort onto the bar.

However, West Ham’s persistence paid off barely 10 minutes later as they went ahead through Kudus.

Alvarez found the ball in midfield, picked his head up and delivered a lofted pass in behind the Freiburg defence for the Ghana international, who finished expertly past goalkeeper Noah Atubolu.

The goal was credit to the hosts’ early pressure and Kudus’ well-timed run and touch tested the VAR, who allowed the effort to stand despite calls for offside and handball.

Last season’s Europa Conference League champions looked eager to finish their opponents off quickly but Jarrod Bowen’s goal was ruled out for offside by referee Joao Pinheiro.

The England winger had got on the end of a similar ball to the one which had previously caught out the Freiburg defence, however he had failed to hold his line and the score remained 1-0.

At the other end, Freiburg, having already qualified from Group A alongside West Ham, rarely ventured as far as West Ham’s box until Ritsu Doan tested Lukasz Fabianski after 40 minutes.

But creator Alvarez turned scorer moments later to seal the tie.

The Mexican marauded forward with the ball and played a neat one-two with Bowen before finishing his work with a poacher’s finish into the bottom corner.

Freiburg showed a bit more fight in the second half through Doan, who rifled an effort at Fabianski, but it was West Ham who were in the ascendancy and looked more likely to strike the next blow.

Czech full-back Vladimir Coufal overlapped on the right flank and delivered a cut-back cross to Bowen who scuffed his effort over the bar instead of finding the empty net.

The dangerous Doan continued to be the only threat for Freiburg when he forced the save from Fabianski before substitute Noah Weishaupt’s rebounded effort was sliced over the bar.

Kemar Roofe’s late goal earned Rangers a memorable 3-2 win against Real Betis to send the Light Blues into the Europa League knockout stages.

Roofe turned the ball home from close range as Rangers put the pressure on from a 78th-minute corner to clinch top spot in Group C.

The Light Blues inflicted a first home defeat of the season on the Spaniards in Seville as Roofe’s second goal of the season saw them jump above Sparta Prague from third place and send Betis into the Conference League.

Abdallah Sima and Cyriel Dessers had each put Rangers ahead in a thrilling first half but Betis were level before the break and had chances to go ahead only to slip from top spot to third.

Sparta won 3-1 against Aris Limassol to put pressure on Rangers and ultimately go through themselves as the Ibrox side did it the hard way, finishing on 11 points despite dropping five against the Cypriots.

Sima had already seen a half-chance diverted wide before opening the scoring in the 10th minute. James Tavernier and then Ross McCausland drove down the right and Dessers helped the ball on for Sima to fire into the bottom corner from 16 yards.

The lead only lasted four minutes. Juan Miranda had put a dangerous ball across the face of goal moments earlier but McCausland did not heed the warning and failed to track the left-back’s forward run. Miranda burst on to a deft flick from Borja Iglesias and drilled the ball inside the far post.

Rangers survived a torrent of pressure as Betis looked to build on their equaliser. Ben Davies produced a vital block,  Andres Guardado hit the underside of the crossbar and Jack Butland tipped over Hector Bellerin’s strike.

Rangers withstood the pressure and regained the lead in the 20th minute, seconds after taking a throw-in inside their own half. Dessers headed inside for Jose Cifuentes and ran on to the return ball down the left wing.

The Nigeria international went a long way to winning over the Gers fans following a slow start to his Ibrox career when he beat his man and slipped the ball through the goalkeeper’s legs.

This time the lead lasted 17 minutes. Rangers were on the back foot after an attacking move broke down but they had plenty of men back, however Tavernier was slow to spot the danger as Ayoze Perez loitered with intent outside the right-back.

The former Newcastle and Leicester striker curled an inch-perfect first-time shot just inside the far post after being set up by Isco.

Sima and Dessers threatened before the break but Rangers – with Dujon Sterling on for Cifuentes – faced pressure at the start of the second period as Betis twice threatened from set-pieces. Assane Diao headed against the crossbar and Marc Roca miscontrolled the ball inside the six-yard box, allowing Butland to block.

Sam Lammers briefly looked like going clear on goal after dribbling past two players but he seemed to go down easily after being tripped just outside the box and Borna Barisic’s free-kick was blocked.

Rangers had another nervy moment waiting on the VAR verdict when Perez had a goal disallowed for handball after bundling home a rebound.

It was Rangers who struck from similar range moments later.

The Light Blues generally managed the latter stages well until late in stoppage-time when substitute Rabbi Matondo in particular showed naivety in shooting from long range, however Butland scrambled to stop Willian Jose’s header creeping in.

The final whistle soon sounded to continue Rangers’ promising run under recently-appointed manager Philippe Clement, who could now get his hands on his first piece of silverware in Scotland after Sunday’s Viaplay Cup final against Aberdeen.