Manchester United crashed out of Europe as a 1-0 home defeat to Bayern Munich on Tuesday night 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 that 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.
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.
Reigning Italian champions, Napoli, also secured their place in the knockout phase by beating Sporting Braga 2-0 at home, with newly crowned African Player of the Year, Victor Osimhen, completing the job after Serdar Saatci’s own goal.
READ ALSO: Bournemouth thrash Man United at Old Trafford, Liverpool win
Napoli finished second behind Group C winners Real Madrid, who had already won the group even before they beat Union Berlin 3-2 in the German capital.
Kevin Volland put Union ahead, but Joselu scored twice for Real and although Alex Kral equalised, Dani Ceballos notched the winner for the 14-time European champions in the 89th minute.
Last year’s beaten finalists Inter Milan finished second after a goalless draw with Group D winners Real Sociedad.
In the early matches, a much-changed Arsenal were held 1-1 at Dutch league leaders PSV Eindhoven but still top Group B.
Eddie Nketiah fired a low shot into the corner to put Arsenal ahead, but Yorbe Vertessen curled in an equaliser.
Sevilla finished bottom of that group after Lens scored a late winner in a 2-1 victory in northern France.
It means the Spanish side won’t even have the chance to add to their seven Europa League titles, with Lens grabbing third place in the group and a Europa League place.
Benfica also secured a late ticket to the Europa League after they beat Salzburg 3-1 in Austria to clinch third place in Group D.
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