The Independent

Rangers will face Jose Mourinho's Fenerbahce in the last 16 of this season's Europa League.

The Scottish club, who finished eighth in the group phase table, have been drawn against the Turkish Super Lig outfit after their 5-2 aggregate victory over Anderlecht which was secured by a 2-2 draw in the second leg of their play-off in Belgium on Thursday evening.

Manchester United's reward for automatic qualification is a showdown with Spanish side Real Sociedad, who put five past Midtjylland to add to their 2-1 win in the away leg as they progressed 7-3 on aggregate.

United, who lifted the trophy in 2017, last met Sociedad in the same competition in 2022-23 when both matches ended 1-0 to the away side.

Premier League counterparts Tottenham Hotspur will lock horns with AZ Alkmaar for the second time this season.

The Dutchmen lost 1-0 in North London during the group stage in October when Richarlison's penalty proved decisive on a night when the visitors had defender David Moller Wolfe sent off with five minutes remaining.

Rangers and Fenerbahce currently lie second in their respective leagues' with Philippe Clement's men 13 points adrift of leaders Celtic and Mourinho's charges six shy of Galatasaray.

They last met in the third qualifying round of the Champions League in 2001, when the Turks progressed courtesy of a 2-1 second leg win in Istanbul after a goalless draw in Glasgow.

For United and Spurs, the competition perhaps represents their best chance of winning a trophy this season.

Spurs are 12th in the Premier League after last weekend's 1-0 win over Ruben Amorim's side, who sit 15th.

The ties will take place on March 6 and 13.

Should Rangers progress, they will face either Roma or Athletic Bilbao in the quarter-final, while United would line up against FCSB or Lyon and Spurs Ajax or Eintracht Frankfurt.

Chelsea, meanwhile, face Copenhagen in the Uefa Conference League.

PA

Tottenham Hotspur will face AZ Alkmaar in the last-16 of the Europa League as their route to the final emerged after Friday’s draw.

Spurs finished an impressive fourth in the new and extended group phase of the competition, meaning they were seeded for the draw in Nyon.

Despite their poor form domestically, Ange Postecoglou’s team finished the group phase strongly with victories over Hoffenheim and Elfsborg.

Tottenham’s last involvement in the competition, in 2020-21, saw them reach the last-16 where they were knocked out by Dinamo Zagreb.

Let’s see how Tottenham could make the final in Bilbao on 21 May.

Who will Tottenham face in the last 16?

Tottenham will face AZ Alkmaar in the last 16.

AZ Alkmaar defeated Galatasaray in the knockout phase play-offs, 6-3 on aggregate.

The draw also confirmed the entirety of the Europa League knockout bracket.

Tottenham know that if they beat AZ Alkmaar in the last-16, they will face either Ajax or Eintracht Frankfurt in the quarter-finals. The first leg would be at the Tottenham Hotspur Stadium.

Should Spurs make it to the semi-finals, they will face either Viktoria Plzen, Lazio, Bodo/Glimt or Olympiacos. The first leg would be at the Tottenham Hotspur Stadium.

The final is on 21 May at the San Mames in Bilbao.

When will Tottenham play their last-16 tie?

Tottenham will play the first leg of their last-16 match away from home at AZ Alkmaar on 6 March and then the second leg at Tottenham Hotspur stadium on 13 March.

Europa League last 16 draw in full

Bodo/Glimt vs Olympiacos

Ajax vs Eintracht Frankfurt

Viktoria Plzen vs Lazio

AZ Alkmaar vs Tottenham

Real Sociedad vs Man Utd

Fenerbahce vs Rangers

FSCB vs Lyon

Roma vs Athletic Club

Round of 16: 6 & 13 March 2025

Quarter-finals: 10 & 17 April 2025

Semi-finals: 1 May & 8 May 2025

The Europa League knockout stage draw has taken place with Manchester United, Tottenham and Rangers learning their last-16 opponents.

The three British representatives are among the strongest sides left in an intriguing competition that feels wide open given the Premier League’s pair respective travails.

Manchester United take on Real Sociedad with both clubs struggling domestically this season, while Tottenham face Dutch opposition in the form of AZ Alkmaar.

Rangers, meanwhile, face a long trip to Turkey and a meeting with Jose Mourinho’s Fenerbahce.

The Europa Conference League draw, which includes Chelsea, follows the second-tier proceedings.

Tottenham Hotspur’s unpredictable season will feature knockout football in the Europa League after Spurs claimed a top-eight place and they’ll discover their opponents this week in Friday’s draw.

Ange Postecoglou’s side sit 15th in the Premier League but the Europa League offers them the chance to end their long trophy drought, and Spurs should stand as one of the favourites when their injury crisis clears.

After winning their first three Europa League fixtures this season, Spurs wobbled and suffered defeat to Galatasaray before dropping points against Roma and Rangers. But a win over Hoffenheim, followed by three points again Elfsborg got Tottenham over the line.

What has been a difficult season for Tottenham could still end with a trophy but their fate now rests on Friday’s knockout draw.

Who Tottenham could face in Europa League last-16

After finishing as the fourth seeds in the league phase, Spurs are paired with third seeds Manchester United in the knockout bracket.

They know they will face either AZ Alkmaar or Real Sociedad. Manchester United will play the other team.

The Dutch side defeated Galatasaray 6-3 on aggregate, while Sociedad defeated Midtjylland 7-3 on aggregate in another high-scoring tie.

When will Tottenham learn their last-16 opponents?

The Europa League draw for the last-16 takes place on Friday, February 21 at 12pm GMT.

When will Tottenham play their last-16 Europa League tie?

The Europa League last-16 takes place across 6 and 13 March. As the seeded team, Tottenham will be home in the second leg.

Europa League draw in full

Viktoria Plzen - to play Lazio or Athletic Club in last-16

Bodo/Glimt - to play Olympiacos or Rangers in last-16

Ajax - to play Eintracht Frankfurt or Lyon in last-16

AZ - to play Man Utd or Tottenham in last-16

Real Sociedad - to play Man Utd or Tottenham in last-16

FSCB - to play Eintracht Frankfurt or Lyon in last-16

Fenerbahce - to play Olympiacos or Rangers in last-16

Roma - to play Lazio or Athletic Club in last-16

The draw for the next round of the Europa League takes place on Friday, with Manchester United and Tottenham Hotspur waiting to learn who they will face in the last 16.

Both clubs have had a torrid time of late in the Premier League, but while positions of 12th and 15th are further evidence that both sides are among the poorest in the Premier League (in relative terms at least), they are the bookies’ favourites to win the Europa League.

Having finished third and fourth respectively in the league phase, Spurs and United have since been placed in opposite sides of the draw, meaning they cannot meet until the final - though one of them will play Real Sociedad in the last-16.

With clubs including a high-flying Athletic Bilbao, league-phase ‘winners’ Lazio and 2022 winners Eintracht Frankfurt still in the competition, any run to the final would certainly be difficult for the English contingent.

And while it will rightly raise eyebrows to call Spurs and United the favourites for a cup tournament at the moment, are there many clubs who could mount a challenge for the tournament, and if so, who are they?

Real Sociedad

Europa League position: 13th

Star player: Martin Zubimendi

Domestic form: 11th, 20 points behind first

One of the biggest challenges to Spurs and United could well come straight away, with both sides able to face Real Sociedad in the round of 16.

The Basque side have struggled in La Liga this season having lost Mikel Merino and Robin Le Normand, but on their day they remain one of the best sides in Spain.

And there is quality throughout the starting eleven, from Liverpool target Martin Zubimendi to Japanese winger Takefusa Kubo and local favourite Mikel Oyarzabal, scorer of the goal that won Euro 2024.

While the latter two will provide plenty of threat to the already stretched English clubs in defence, the midfield trio of Zubimendi, Pablo Marin and Brais Mendez can also hurt the English sides in central areas.

A win over Barcelona and a draw with Atletico Madrid earlier this season show that the Basque outfit can go toe-to-toe with the continent’s best sides, and with Spurs and United’s other opponent potentially being AZ Alkmaar, both sides will likely want to avoid the trip to San Sebastian.

Athletic Bilbao

Europa League position: 2nd

Star player: Nico Williams

Domestic form: 4th, six points behind 1st

Athletic Club are probably the biggest threat to the English sides, for a number of reasons – not least because they will be desperate to make the final at their home stadium.

The combination of pace and creativity across the front line could expose the English clubs, while their defence – which is the second best in the league, having conceded just 21 league goals so far this season – will be hard to break down.

The Basque side are just six points behind Barcelona and are arguably in the La Liga title race, with star players including the Williams brothers – long-time favourite Inaki and Spain star Nico – as well as emerging young talent Oihan Sancet.

With the club having built on last season’s brilliant Copa del Rey win to mount an unlikely charge for the top four (or title), their season-long form suggests that Bilbao will have enough to threaten both United and Spurs.

Lazio

Europa League position: 1st

Star player: Valentin Castellanos

Domestic form: 5th, 10 points behind 1st

The Serie A side finished top of the league-phase table with six wins, one draw and one loss, having beaten sides including Ajax, Porto and Real Sociedad. They will face Viktoria Plzen or Roma in the round of 16.

On paper, the squad is perhaps less talented than those of Bilbao or even Frankfurt, and it is certainly a far cry from the multi-million pounds teams assembled by Spurs and United, with ex-Chelsea man Pedro and 26-year-old striker Valentin Castellanos among the Rome-based side’s key players.

Lazio have lost seven matches so far in Serie A this season, and though they sit in fifth, they have done little to suggest that they can beat the very best sides over two legs.

Nevertheless, we aren’t talking about the ‘very best’ when referencing Spurs and Man Utd, and Lazio’s form against clubs like Ajax and Porto proves that they can cause problems.

Both English clubs could meet the Biancocelesti in the quarter-finals in theory, so it may be a match-up we see soon. If so, a lot could depend on whether the Premier League sides have welcomed back key players from injury – if they have, they should both have enough to beat the Italians, despite what’s been on show domestically.

Eintracht Frankfurt

Europa League position: 5th

Star player: Hugo Ekitike

Domestic form: 3rd, 13 points behind 1st

Frankfurt won this competition in 2021/22 and have kicked on from there, finishing progressively higher in the Bundesliga and now occupying third place this season.

The squad was weakened by the loss of their best player when Manchester City completed the signing of Omar Marmoush in January, but in the Egyptian’s absence, former PSG striker Hugo Ekitike has taken on the mantle of star player, with the Frenchman having scored 17 goals so far this season.

While their domestic form suggests that they have the ability to cause problems for any side in the competition, a loss to Lyon and a draw to Viktoria Plzen show that the German side can leak goals against better sides.

In addition, three successive league draws since the loss of Marmoush show that the team is still trying to gel after the loss of their talisman, and while both Spurs and United could be troubled by the Bundesliga side, either should have enough to go through given the nature of two-legged ties.

Lyon

Europa League position: 6th

Star player: Rayan Cherki

Domestic form: 6th, 20 points behind first

The French side’s domestic form has improved drastically over the last year or so, and they now sit sixth in Ligue 1, albeit nowhere near challenging for the title.

Their European campaign was stained by a loss to Besiktas and draws with Hoffenheim, Fenerbahce and Ludogorets, but the seven-time Ligue 1 champions have plenty of quality throughout the side, and certainly enough to win two matches.

Rayan Cherki remains the side’s most notable player, as he is capable of the spectacular in terms of both goals and assists. And in Georges Mikautadze they have Euro 2024’s joint-top scorer, while the midfield trio of Jordan Veretout, Nemanja Matic and Corentin Tolisso are more than capable of giving their side the edge over two legs, especially against the weakened midfields of Spurs and United.

Tottenham Hotspur’s unpredictable season will feature knockout football in the Europa League after Spurs claimed a top-eight place and they’ll discover their opponents this week in Friday’s draw.

Ange Postecoglou’s side sit 15th in the Premier League but the Europa League offers them the chance to end their long trophy drought, and Spurs should stand as one of the favourites when their injury crisis clears.

After winning their first three Europa League fixtures this season, Spurs wobbled and suffered defeat to Galatasaray before dropping points against Roma and Rangers. But a win over Hoffenheim, followed by three points again Elfsborg got Tottenham over the line.

What has been a difficult season for Tottenham could still end with a trophy but their fate now rests on Friday’s knockout draw.

After finishing as the fourth seeds in the league phase, Spurs are paired with third seeds Manchester United in the knockout bracket.

The knockout play-off ties were drawn on Friday with the 13th, 14th, 19th and 20th seeds now facing off for a right to make it into next month’s draw. The winners will they face United or Spurs.

Those ties are Real Sociedad vs Midtjylland and Galatasaray vs AZ Alkmaar.

The Europa League play-offs take place across 13 and 20 February. As the seeded teams in the play-off draw, Real Sociedad and Galatasaray will play the second legs at home.

The draw for the last-16 then takes place on February 21.

The Europa League last-16 takes place across 6 and 13 March. As the seeded team, Tottenham will be home in the second leg.

Ferencváros vs Viktoria Plzen - to play Lazio or Athletic Club in last-16

Twente vs Bodo/Glimt - to play Olympiacos or Rangers in last-16

Union Saint-Gilloise vs Ajax - to play Eintracht Frankfurt or Lyon in last-16

AZ vs Galatasaray - to play Man Utd or Tottenham in last-16

Midtjylland vs Real Sociedad - to play Man Utd or Tottenham in last-16

PAOK vs FSCB - to play Eintracht Frankfurt or Lyon in last-16

Fenerbahce vs Anderlecht - to play Olympiacos or Rangers in last-16

Porto vs Roma - to play Lazio or Athletic Club in last-16

Towards the end of Tottenham Hotspur’s 1-0 win over Manchester United, with the game still in the balance, both Brennan Johnson and Patrick Dorgu lost theirs. The two players careered into each other, leaving them both on the floor.

It was a moment to sum up what must have been one of the worst Premier League matches ever played, relative to the cost of both squads. This isn’t to criticise either player, or any of the players, or even the managers.

It is just the peculiar context that both clubs find themselves in, with the match preceded by a Spurs supporters protest against the ownership. Their team at least got a win that matters more to them, with Ange Postecoglou talking about how “it was important for us” (and certainly for him). But it’s hard to know what any of it means for United. Maybe nothing. That’s what the season has become.

Their Premier League campaign is another write-off, perhaps worse than 2021-22 and the most pronounced since 1988-89. Sir Alex Ferguson’s early United finished 11th that season, with a mere 45 goals in 38 games. Right now, it’s 15th and 28 in 25. This defeat was actually the 10th game in the Premier League that United haven’t scored in. That’s 40 per cent of their matches.

You can see why Ruben Amorim wanted to come at the end of the season rather than midway through it. “My job is so hard,” he said, after United’s 12th defeat of the league campaign.

It has been said on these pages before, but there’s an argument to just totally write the campaign off and use it positively as preparation for next term.

It’s hard not to think like that when the situation has somehow got worse. Having necessarily reduced the numbers in their squad over the transfer window despite badly needing reinforcements, United now have both Amad Diallo and Kobbie Mainoo injured for lengthy spells. Amad, who has been one of the few sources of hope this season, is now expected to miss the rest of it. Amorim spoke hopefully that Mainoo may only miss weeks rather than months.

Postecoglou naturally expanded on this theme after the game, saying he could empathise – but, tellingly, not sympathise.

“I could see Ruben there, players out of position, kids on the bench... welcome to my world,” Postecoglou said. “But that’s for one game. Do that for two months. Do that for two months. And that’s anyone.”

The Spurs manager then insisted such injury crises could affect anyone. Little doubt about where Postecoglou was pinning responsibility for this. He was pointing to the calendar, rather than issues with any individual club or managerial approach.

“What’s happened to us is going to happen to other clubs,” Postecoglou said, “and it’s coming.”

Here, James Maddison coming back from injury proved decisive, as he scored the game’s only goal. It had all the more resonance since Roy Keane had made headlines this week for strident criticism of the playmaker. Maddison made play of that in his celebration, referencing the darts that had been brought up and “shushing” the noise.

Keane might well counter that this was a match between 13th and 14th, rather than a game of any great significance to the Premier League table.

It wasn’t really like the goal was a product of exemplary attacking play, either. United were getting caught out by wide balls, Son Heung Min swung a cross back and then Andre Onana spilled a shot at Maddison’s feet.

The playmaker did well to be there, which you could say was important given that mere presence – literally being there on the pitch – was such a crucial differential.

It otherwise stood out because the game was mostly defined by low-quality attacking cancelling out low-quality defending. There was so much space, but no one really had the quality to do much with it.

Most of the more memorable shots seemed to fly waywardly over the bar rather than even test the goalkeepers. Hence another defining moment featured Joshua Zirkzee missing a volley completely at the back post. As with Johnson and Dorgu, though, this isn’t to single out Zirkzee.

The Dutch forward actually offered most of United’s more productive moments, and you could see how he would be a useful option – especially as a link player – in a good team. In a team like this, though, it’s just too much responsibility to bear. The same with Rasmus Hojlund, and even Alejandro Garnacho.

It’s almost unfair on them, and raises such questions about the club’s recruitment over the past two to three years.

And yet what can the manager do? Performances like this will inevitably bring more scrutiny on Amorim, as people reasonably start to point out the bare facts. In his time, United have become worse. Some selection decisions have been baffling.

That would be a superficial reading, though. The truth is that United, as a club, had bottomed out. A series of bad decisions left them at a point where everything now just needs to be rebuilt.

It’s why this season’s games almost have to be used as tactical building blocks. Hence it doesn’t feel as damning that Amorim doesn’t offer more pragmatism for individual games like this, when injuries are so bad. Casemiro, for one, need not have been so tactically exposed.

Amorim himself understandably dodged a question on whether this campaign should almost be seen as an extended pre-season. He can’t afford to let his players think like that, after all, and he still has two cup competitions to try and win. That is something else that’s reminiscent of the 1980s or early 1990s.

Amorim did admit United are in a kind of “survival” mode, where it is just about seeking to improve individual aspects for the next game.

It instead feels like purgatory. A lot of this match was the same.

There’s not even much to read into it. This doesn’t tell us anything meaningful about Amorim’s capacity to manage United, because this just isn’t what United should be or anything like his idealised team.

This is the point about preparing for next season.

The problem with such idealising is that the reality of it is extremely grim. It’s also where clubs do have to look to the bigger picture. It's where they have to show patience, and a bit of nerve.

Postecoglou may empathise with that, too. He can now hope that Spurs have come through their own crisis, as players return and they claim successive Premier League wins for the first time since November. They got through it.

Many who watched this game might feel the same. It was not, as the saying goes, an advertisement for the Premier League. It was instead a showcase of wider issues, from ownership to the calendar.

Tottenham Hotspur fans turned out in numbers to protest against chairman Daniel Levy and the club’s ownership before Sunday’s home fixture with Manchester United.

Frustration amongst supporters has increased throughout a difficult winter period and last week saw Ange Postecoglou’s injury-hit team crash out of the Carabao Cup and FA Cup in the space of 72 hours.

Fan group Change for Tottenham had already arranged a protest for the visit of United and a crowd of at least two thousand made their way down the High Road before they congregated outside the stadium where various chants for Levy to leave the club followed.

A number of banners were held up as fans gathered outside the West Stand.

The largest – aimed at majority owners ENIC – read: ‘24 years, 16 managers, 1 trophy – Time for change’.

Another banner said: ‘Our Game Is About Glory, Levy’s Game is About Greed’.

Earlier this week Change for Tottenham member Christina Zandes told the PA news agency: “Even if we do get a win on Sunday, it doesn’t matter – we still want change to happen.

“This cycle is on repeat and we can’t keep going on with this. We’re tired.

“A lot of the fans are disconnected completely from the club and it’s a horrible feeling to see how bad we’re struggling right now and it should not be happening.”

Frustration has often centred on Tottenham’s lengthy trophy drought, with the 2008 League Cup their last silverware.

Data released by financial experts Deloitte last month has also been used against chairman Levy and ENIC.

Spurs placed ninth in Deloitte’s list of the world’s richest clubs with revenue of £520m from the 2023-24 season, but the club’s spend of 42 per cent of its revenue on wages was the lowest of any team in the top 10. It was also lower than all eight Premier League clubs in Deloitte’s top 20 with West Ham, Newcastle and Aston Villa spending more of their revenue on wages.

While Spurs signed Dominic Solanke for £65m from Bournemouth last summer alongside a number of highly-rated teenage prospects, it has failed to translate into consistent results with Postecoglou’s squad unable to cope with the demand of extra cup fixtures.

Tottenham went on to claim a 1-0 victory against Manchester United thanks to James Maddison’s 13th-minute goal, but a small crowd of around 200 fans stayed behind at full-time to hold up banners and continue calls for Levy to leave the club in the South Stand.

When Postecoglou was quizzed on the protest, the 59-year-old highlighted the strong backing of the supporters during a vital win.

“Well, I mean, obviously I wasn’t outside so I can’t comment on that, but I thought the fans were great today in the stadium,” Postecoglou said.

“I thought they got behind the team and it was important. Like I said it was an important game for us.

“All the the fans contributed to us getting the result we needed.”

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