Manchester United crashed out of Europe as a 1-0 home defeat to Bayern Munich on Tuesday rounded off a miserable Champions League campaign for the Red Devils.
Kingsley Coman scored the only goal for the Bundesliga champions, who had long since secured their place in the last 16, to leave United without even the consolation of dropping into the Europa League.
An embarrassing early exit from Europe's elite competition increases the pressure on manager Erik ten Hag with United also languishing in sixth in the Premier League.
The damage to United's Champions League hopes was done long before the arrival of Bayern when they failed to win three of their four games against Copenhagen and Galatasaray.
Copenhagen beat Galatasaray 1-0 on Tuesday to join Bayern in the last 16, with the Turkish giants finishing third.
It is just the fourth time than an English side has finished bottom of their Champions League group.
A troubled season for Ten Hag reached a new low on Saturday when Bournemouth won for the first time at Old Trafford and with ease in a 3-0 victory.
The former Ajax boss responded by recalling Raphael Varane to the starting line-up for the first time in nearly two months.
The Frenchman has been surprisingly frozen out by Ten Hag, but is likely to have a big part to play in the coming weeks as Harry Maguire and Luke Shaw had to be replaced during Tuesday's action, adding to an already lengthy injury list.
Bayern were already assured of progressing as Group A winners but Thomas Tuchel's men had a point to prove themselves after suffering a 5-1 hammering at Eintracht Frankfurt on Saturday.
Harry Kane started on his return to England and played a decisive role in the winning goal as he teed up Coman to blast past Andre Onana.
Bayern remain unbeaten in the Champions League group stages since 2017, and extended a competition record of nine consecutive away wins at this stage of the competition.
Yet the German giants rarely had to get out of second gear as they look forward to the knockout stages in 2024.
There was no such excuse for United's lack of urgency as they bowed out with a whimper.
The decision to pursue the potential of Rasmus Hojlund instead of launching a bid for Kane in the summer transfer window looks ever more questionable.
Hojlund is yet to score in the Premier League and has only netted in one of his last 13 United appearances.
Injuries to Marcus Rashford and Anthony Martial meant the young Dane was Ten Hag's only available striker.
Shaw's long-range effort that Manuel Neuer comfortably batted behind was United's only shot on target.
But the loss of Shaw at half-time and Maguire during the first half, to an apparent groin injury, only added to Ten Hag's woes ahead of a daunting trip to Liverpool on Sunday.
United did have one big chance to go in front early in the second half, but Bruno Fernandes' wild effort that flew well over the bar summed up his side's lack of quality and composure in the final third.
Bayern were also far from their free-flowing best.
However, they needed just one slick move to win the game as Kane flicked Thomas Mueller's pass into the path of Coman to fire home his fifth goal of the season 19 minutes from time.
