Champions League PIX: Barcelona crash out; Chelsea, United held

Images from the UEFA Champions League matches played on Wednesday night.

Barcelona crash out of Champions League after Bayern loss

Barcelona crashed out of the Champions League following a 3-0 defeat at Bayern Munich on Wednesday, failing to make it past the group stage of the competition for the first time since the 2000-01 season.

First-half goals from Thomas Mueller and Leroy Sane put the Germans, who won all six matches to top Group E, firmly in the driving seat before Jamal Musiala tapped in the third just past the hour.

Barcelona had advanced to at least the round of 16 every time they competed in the Champions League since 2001 but will continue in the second tier Europa League after ending up third in the group. Benfica qualified as group runners-up with a win over bottom club Dynamo Kyiv.

Barca, who made not a single chance in the second half and scored just twice in six group games, have lost their last two matches in all competitions following new coach Xavi's first defeat in charge of the side by Real Betis on Saturday.

"Bayern were better, superior," Xavi said. "This is the harsh reality we have to face. I have told players that this is a turning-point. Today a new era begins and we have to take Barca where it deserves which is not the Europa League.

"I am frustrated because this is our reality. We start from scratch and we have to get Barca back to fighting for the Champions League. I now feel responsible. Now we have to go out and win the Europa League."

Despite having secured top spot in the group, Bayern coach Julian Nagelsmann fielded his strongest possible team, refusing to rest top players after they beat Borussia Dortmund 3-2 in the Bundesliga on Saturday.

The German champions had been struggling defensively, keeping just one clean sheet in their last eight matches prior to Wednesday.

Jordi Alba tested Bayern keeper Manuel Neuer with a long-range effort in the seventh minute and Ousmane Dembele fired over the bar as the Spaniards initially pressed high. But that was all that was to come from the Barca attack for the rest of the game as the Germans gradually took control.

A scintillating Mueller run down the left caught Barca napping but his cutback came just too late for Robert Lewandowski who failed to tap in from a metre.

The roles were reversed with Lewandowski chipping the ball into the box and Mueller heading in his 50th Champions League goal in the 34th minute, becoming only the eighth player in Champions League history to reach that mark.

Bayern scored again before the break with a Sane missile from 25 metres out. Barcelona, who needed a win to advance, failed to carve out a chance in the second half before Musiala's 62nd minute tap-in sealed their exit.

Benfica progress to last 16 at expense of Barcelona

Benfica stormed into the last 16 of the Champions League with a comfortable 2-0 home win over Dynamo Kyiv on Wednesday, qualifying at the expense of Barcelona.

The Portuguese side took a deserved lead in the 16th minute when Ukrainian striker Roman Yaremchuk met a Joao Mario cross at the near post to score against his former club.

Things got even better for the hosts in the 22nd when Brazilian Gilberto pounced on a botched clearance from Dynamo's Benjamin Verbic and slammed the ball in with one touch.

Benfica finished second in Group E on eight points to reach the Champions League knockout stage for the first time in five years, while Dynamo came bottom with one. Group winners Bayern Munich ended with a maximum 18 points after beating third-placed Barcelona 3-0.

Chelsea lose top spot after 3-3 draw at Zenit

Champions League holders Chelsea finished as Group H runners-up after conceding a stoppage-time equaliser in a pulsating 3-3 draw at Zenit St Petersburg on Wednesday.

The result left Chelsea second on 13 points from six games, two behind group winners Juventus who leapt into pole position thanks to a 1-0 home win over Sweden's Malmo.

Both sides had already booked their last-16 berths while third-placed Zenit will go into the second-tier Europa League after the winter break.

Chelsea made a perfect start as Timo Werner fired them ahead in the second minute with a tap-in after a Ross Barkley corner was nodded into his path.

Mason Mount squandered a sitter to double the lead after Zenit twice came close to an equaliser and the England midfielder's miss turned out to be costly as the home side turned the game round with two quickfire goals.

Brazilian forward Claudinho levelled in the 38th with a glancing header into the far corner after his compatriot Douglas Santos swung in a cross past a static visiting defence.

Rattled by the equaliser, Chelsea fell behind three minutes later when Iranian striker Sardar Azmoun beat the offside trap from Malcom's fine through ball and slotted home after rounding goalkeeper Kepa Arrizabalaga.

Romelu Lukaku hit back in the 62nd minute as he stroked the ball into an empty net after a flowing move and Chelsea seemed to have forced the final twist after Werner struck again in the 85th thanks to more crisp-one touch passing.

The move left Zenit's defence bedazzled with Christian Pulisic delivering the final pass to Werner, who fired in a snap shot from 10 metres after side-stepping his marker.

The Premier League side were undone, however, by a spectacular equaliser at the death as they failed to clear a cross and Magomed Ozdoev unleashed an unstoppable volley into the top corner from the edge of the penalty area.

Second-string Man United held by Young Boys

A second-string Manchester United were held to a 1-1 draw with Switzerland's Young Boys in Champions League Group F in a poor quality match at Old Trafford on Wednesday.

United were already assured of top spot in the group and a place in the last 16 while Young Boys finished bottom and were eliminated.

With little at stake, interim United manager Ralf Rangnick made 11 changes from the team which beat Crystal Palace on Sunday and if it was a chance for some of those left out of recent line-ups to stake their claim, few would have impressed.

Rangnick's preference for high-intensity pressing football had been evident in the win over Palace but this, perhaps understandably given the unfamiliar selection, was a ramshackle display.

One of those who did make a case for a starting place was Mason Greenwood and it was the forward who gave United the ideal start, producing a super volley from a Luke Shaw cross to put the home side ahead in the ninth minute.

Rangnick called Greenwood a "massive talent", praising him also for the work he did to set up Juan Mata for a chance for a second goal which the Spaniard was unable to make the most of the opportunity.

United were sloppy, though, and conceded several openings for David Wagner's Swiss side who drew level three minutes before the interval.

United's Dutch midfielder Donny van de Beek, one of those who need to impress, poorly gave away the ball on the edge of his own box and Fabian Rieder curled it into the corner.

United struggled to find any fluency after the break and Young Boys wasted several chance to win the game, most noticeably when Quentin Maceiras was found in space on the penalty spot but poked his shot wide.

Rangnick, who had handed starts to youngsters Amad Diallo and Anthony Elanga, introduced four academy products after the break included Charlie Savage, the 18-year old son of former Leicester City and Wales midfielder Robbie.

"There were quite a few debuts and game time for players who desperately need game time. I wouldn't say I was happy but it was okay," Rangnick said of the performance.

"I was fully aware before the game that with this team that we played today, we haven't played together as team. The first half hour we did quite okay. We had a few unforced errors but had control of the game. We should have been 2-0 or 3-0 up. We had some great opportunities but we didn't score," he said.

But Rangnick was irritated by the way United had tried to play out from the back.

"What was a little bit annoying was we gave the ball away and played too many balls into the first line of their (pressing) area. Whenever we played the ball into the second or third line, we always made (danger). I told them that before the game but they still played into that first line," he said.

Second place in the group will not be decided until Thursday after the match between Atalanta and Villarreal was postponed because of heavy snow in Bergamo, Italy.

Juventus sneak into top spot with win over Malmo

Juventus progressed to the Champions League knockout stages as group winners after their comfortable 1-0 victory over Malmo on Wednesday, coupled with Chelsea's draw at Zenit St Petersburg.

A much-changed Juventus, already assured of their place in the knockout stages, raced into an 18th-minute lead when Moise Kean headed his first Champions League goal from an inch-perfect Federico Bernardeschi cross.

With Malmo guaranteed to finish bottom of the group, the Swedes had little incentive to push for a leveller and Juve closed out the win without ever being seriously troubled.

The Italian side's fifth win from six group games looked to be in vain as England's Chelsea led 3-2 in Russia in stoppage time, but a last-gasp Zenit equaliser meant Juve finished two points clear at the top of the group.

Okafor strike sees Salzburg to historic win over Sevilla

Noah Okafor scored the only goal as RB Salzburg claimed a 1-0 victory over 10-man Sevilla at the Red Bull Arena on Wednesday to progress to the knockout stages of the Champions League for the first time in their history.

Salzburg finished as runners-up in Group G with 10 points from their six matches, one behind pool winners Lille. Sevilla ended in third place and will play in the Europa League playoff round.

The first half had little goal-mouth action but the game burst into life after the break as Salzburg were helped by a second yellow card for Sevilla’s key midfielder Joan Jordan on 65 minutes.

The match was played behind closed doors without fans due to heightened COVID-19 restrictions in Austria, so the hosts were unable to celebrate their achievement with their supporters.

"I will certainly never forget this game, it is unbelievable what we have achieved over 90 minutes today," Salzburg captain Andreas Ulmer told reporters.

"Everyone supported everyone, and the players who came on as substitutes were also very important. This is a very big moment for Austrian football."

For two sides with reputations as attacking teams, it took 35 minutes of cagey football for the first shot on target as Ivan Rakitic warmed the palms of Salzburg goalkeeper Philipp Kohn.

It was the only occasion when either keeper was tested in the first half, though Sevilla defender Jules Kounde headed wide from a corner with the best chance of the opening period.

Sevilla should have been ahead minutes after the break when Munir El Haddadi had a free header six yards from goal but saw his effort come back of the crossbar.

It was a big chance the visitors would rue missing as Salzburg went up the other end and scored with an excellent team goal.

They finally managed to string passes together and Karim Adeyemi was worked into space on the left. His low cross into the box was turned in by Swiss forward Okafor.

Sevilla’s night got worse on 65 minutes when Jordan received a deserved second booking for pulling back the pacey Adeyemi and they were left needing to find two goals with 10 men.

Salzburg were able to comfortably hold out to the end, with Rakitic’s first-half shot the only one Sevilla, who are second in Spain's LaLiga, could muster on target.