Manchester United have been eliminated from the Champions League and Europe altogether after suffering a narrow 1-0 defeat to Bayern Munich in their final Group A fixture at Old Trafford on Tuesday night.
The Red Devils entered this pivotal contest needing to beat the Bavarian giants as well as hope that Group A rivals Copenhagen and Galatasaray played out a draw in Denmark to have any chance of progressing to the last 16.
However, Erik ten Hag's side finished a bitterly disappointing group-stage campaign on a whimper as they boasted just one shot on target against a Bayern side who claimed maximum points courtesy of a 70th-minute strike from Kingsley Coman.
Man United's defeat coupled with Copenhagen's 1-0 win over Galatasaray means that the Red Devils have finished bottom of the group for just the second time in the Champions League, previously doing so in 2005-06, after accumulating just four points from a possible 18 available.
Bayern had already qualified for the last 16 as Group A winners, but nevertheless strengthened their lead at the summit with victory at Old Trafford – their first success on the red side of Manchester since April 2001 when they also won by a 1-0 scoreline.
As for Copenhagen, a surprise package in this season's group stage, they will join Thomas Tuchel's side in the knockout rounds after securing second spot, meaning that Galatasaray finish third and will enter the Europa League playoff round.
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Ten Hag made two changes to the Man United side that suffered a 3-0 Premier League loss to Bournemouth last weekend, with Raphael Varane and Rasmus Hojlund recalled at the expense of Sergio Reguilon and Anthony Martial, the latter of whom was absent due to illness along with Marcus Rashford.
Meanwhile, Tuchel made just the one change to the Bayern side that surprisingly lost 5-1 by Eintracht Frankfurt in the Bundesliga last time out, with Eric Maxim Choupo-Moting replaced by Jamal Musiala.
In front of a fired-up Old Trafford crowd, Man United were given an early warning sign of Bayern's threat inside the first two minutes when Harry Kane burst down the right channel and whipped a dangerous delivery across the six-yard box that former Manchester City man Leroy Sane could not reach.
Man United made a promising start to proceedings otherwise as Bayern initially looked passive, but the Red Devils ultimately failed to test Manuel Neuer between the sticks until the 23rd minute when Luke Shaw fizzed a left-footed shot straight down the throat of Bayern's No.1, who had to punch the ball behind for a corner.
Ten Hag's side were then forced to put their bodies on the line at the other end as Harry Maguire and Diogo Dalot both blocked efforts from Sane and Musiala following a brilliant one-two between the skillful Bayern pair on the edge of the penalty area; Sane then missed another decent chance a few minutes later from close range as he failed to connect with an inviting Coman cross.
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Man United were dealt a huge injury blow shortly before half time as in-form centre-back Maguire was forced off with an apparent groin problem, with 35-year-old Jonny Evans brought on to partner Varane at the heart of the defence.
Ten Hag will have been pleased with how his Man United side managed the game and looked defensively compact in the first 45, but they were lacking a real spark in the final third and struggled to get the best out of Hojlund, who cut an isolated figure up front.
Luke Shaw appeared to sustain an injury before the end of the first half and he was subsequently replaced by right-back Aaron Wan-Bissaka at the break, with Dalot switching over to left-back as a result; Bayern, meanwhile, replaced Noussair Mazraoui with Konrad Laimer.
Bruno Fernandes was presented with a decent opportunity to test Neuer just three minutes into the second half, but the United skipper leant back and fired a poor first-time strike high over the crossbar from the edge of the area.
Alejandro Garnacho then fizzed in a dangerous delivery from the left towards Scott McTominay and Antony inside the six-yard box, but Kim Min-jae was there to slide across and clear the ball from danger.
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Bayern were not quite at their best and rarely threatened Andre Onana in Man United's goal, but they eventually broke the deadlock 20 minutes from time courtesy of a close-range finish from Coman.
A fantastic flick from Kane with the outside of his right foot on the edge of the area put Coman through on goal, and the French winger kept his cool to smash a right-footed strike beyond Onana with aplomb to silence the Old Trafford faithful.
Ten Hag was lacking real game-changers on his bench and only had Hannibal Mejbri, Facundo Pellistri and Kobbie Mainoo to call upon in an attempt to restore parity in the closing stages, but the Red Devils failed to pose a threat in the final third and they eventually slumped to their seventh home defeat of the season in all competitions.
Man United will look to quickly dust themselves down as they prepare for Sunday's daunting trip to Anfield to face Premier League leaders Liverpool, while Bayern will look to build on their success at Old Trafford when they play host to Stuttgart in the Bundesliga.
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