Jeers rang out around Old Trafford as Manchester United was eliminated from the Champions League on Tuesday after a 1-0 loss at home to Bayern Munich.
Kingsley Coman scored in the 70th minute to end the three-time European Cup winners' slim chances of advancing to the knockout stage.
A 12th defeat of the season in all competitions meant United could not even secure the safety net of a place in the Europa League after finishing bottom of Group A. Copenhagen advanced to the round of 16 behind group winner Bayern after beating Galatasaray 1-0.
That result meant even a United win would not have seen it advance to the next stage. And an embarrassingly early exit is the latest setback in a troubled campaign for manager Erik ten Hag.
Injury to Harry Maguire added to his concerns ahead of Sunday's Premier League game at leader Liverpool.
Fans made their feelings known as the final whistle blew on another disappointing night for United, while Bayern fans taunted their rivals.
The odds had always been stacked against United after managing just one win in the group stage going into its final game.
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Ten Hag’s team had to end Bayern’s tournament record 39-game unbeaten run in the group stages and still hope for a draw between Copenhagen and Galatasaray to take the runner-up spot.
Bayern may have already been assured of top spot in the group and a place in the knockout stage for the 16th straight season, but it showed no sign of taking the game lightly and looked assured for much of it.
United’s prospects weren’t helped when, shortly before halftime, Maguire was substituted because of an apparent groin injury. Jonny Evans replaced the England international.
Another defender, Luke Shaw, was then substituted at the break, with Aaron Wan-Bissaka coming on in his place.
Bayern had created the better chances in the first half, with Leroy Sane the visitors’ biggest threat. But he got technique all wrong with an attempted side-foot volley from close range that failed to hit the target.
United’s best opportunity came through Shaw's long shot that was punched over by Manuel Neuer.
In a game of few chances, Bayern broke the deadlock with a goal of real quality.
Coman had harried United’s defenders as the home team struggled to play out from the back. When the ball broke loose, substitute Thomas Muller flicked it to Kane, who played an incisive pass into the run of Coman.
With only Andre Onana to beat, the forward powered a shot into the bottom corner.
Ten Hag made a host of changes in an attempt to find an equalizer that never looked likely as Bayern comfortably saw out the win.
