Jeers rang around Old Trafford on Tuesday as Manchester United suffered an embarrassingly early exit from the Champions League after a 1-0 loss to Bayern Munich.
Kingsley Coman's 70th-minute goal ended the three-time European Cup winners' slim chances of advancing to the knockout stage and delivered a latest blow in an ever-worsening season for Erik ten Hag.
The 12th defeat in all competitions this season meant United could not even secure the safety net of a place in the Europa League after finishing bottom of Group A.
"The facts are we do not have enough points, we are disappointed as a group, as a manager, I am disappointed. We should have done better," Ten Hag said.
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.
Injury to Harry Maguire only added to Ten Hag's concerns ahead of Sunday's Premier League game at leader Liverpool, with the pressure mounting on the Dutchman.
United never looked like getting the win it needed after registering just one shot on target — a long-range effort from Luke Shaw — in the entire match. And fans made their feelings known as the final whistle blew on another disappointing night for Ten Hag's team, while Bayern supporters revelled in taunting their rivals.
"Sometimes you feel pretty lonely as a coach," Bayern coach Thomas Tuchel said.
It was only the second time that United has finished bottom of its Champions League group and the third occasion it has failed to advance to the knockout stage in seven attempts since former manager Alex Ferguson retired in 2013.
A record of 15 goals conceded in the group stage is the most by any Premier League team in the competition's history, according to Opta stats.
The odds had always been stacked against United after managing just one win in the group going into its final game.
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.
But United barely troubled a Bayern team that had already been assured of top spot in the group and a place in the knockout stage for the 16th straight season.
"We had our moments but just didn't take them," Ten Hag said.
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, 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 shot that was punched over by Manuel Neuer.
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 to seal another painful defeat for Ten Hag.
As Tuchel looks ahead to the round of 16 and the potential of challenging for the title when the competition resumes next year, he spared a thought for his opposite number.
"Almost always I feel sympathy for the other coach but, of course, within the competition we try everything to win matches," he said. "These are the rules of high level sports and of sports in general."
