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.
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.