MANCHESTER UNITED suffered European heartache at the hands of RB Leipzig in the Champions League last night.
The Red Devils had begun their Group H campaign by winning in Paris and battering RB Leipzig at Old Trafford.
But a series of poor performances led to their demise, which was capped off by the Germans last night.
Their disappointment, however, is far from the worst suffered by English clubs on the continent.
Let’s take a look at five particularly awful nights for Premier League clubs in Europe.
TOTTENHAM 2 BAYERN MUNICH 7 – 2019
Let’s kick off with a recent one.
Spurs went into this mouthwatering group stage clash as the previous season’s finalists, while Bayern were aiming to lay down a marker – despite having struggled in the league under Niko Kovac.
Things actually started brightly for the Lilywhites, as Son Heung-min fired them into a 12th minute lead.
But Joshua Kimmich pegged them back three minutes later, before the clinical Robert Lewandowski pounced on the stroke of half time to make it 2-1.
Tottenham collapsed in the second half, however, leaking three goals in the final seven minutes as former Gunner Serge Gnabry returned to North London to torment his former rivals.
Bayern went on to win the competition, while Spurs limped out against RB Leipzig in the round of 16.
ARSENAL 1 BAYERN MUNICH 5 – 2017
Before they turned their attentions toward Spurs, Bayern took immense joy in embarrassing Arsenal year after year.
The Bavarians knocked Arsene Wenger’s side out at the round of 16 stage in 2013 and 2014.
Gunners fans had temporary respite, when they beat Bayern 2-0 at the Emirates in the group stage the following season.
But it only served to rile their opponents, as they were promptly battered 5-1 in the away fixture.
Bayern took the humiliation a step further when they drew each in the round of 16 yet again in 2017, beating the Gunners 5-1 in the first leg at Allianz Arena.
And they topped it off by trouncing them 5-1 for a third time in the return leg in North London – as goals from Robert Lewandowski, Arjen Robben, Douglas Costa and Arturo Vidal turned Wenger’s final Champions League match as a manager into a miserable one.
DINAMO BUCHAREST 5 EVERTON 1 – 2005
After a decade in the doldrums since their FA Cup win in 1995, Everton fans rejoiced when they managed to qualify for the Champions League in the 2004-05 season.
Things were immediately slightly tainted, by bitter rivals Liverpool winning the whole thing just days later.
And then it got even worse, when the Toffees were eliminated in the qualifying round by Villarreal.
David Moyes’ men plunged in the Uefa Cup, but still needed to win a round to get into group stage.
But they failed spectacularly, as they were humiliated in Romania,
Dinamo took the lead on 27 minutes, but Joseph Yobo managed to equalise just three minutes later.
But things fell apart in the second half, as a side featuring the likes of Tim Cahill and Phil Neville conceded FOUR times after the break.
Cahill managed to strike in a 1-0 win in the second leg at Goodison Park, but the damage was already done and Everton crashed out of Europe altogether before October.
ARSENAL 1 AS MONACO 3 – 2015
For once, the Gunners thought they had bagged a great Champions League round of 16 draw in Monaco, having taken a gap year from having to face Bayern Munich.
The little fancied French side had managed to top their group ahead of Bayer Leverkusen, Zenit Saint Petersburg and Benfica, but no-one really thought they’d be a match for the Gunners.
But they took the lead in the 38th minute through Geoffrey Kondogbia.
And things got even worse eight minutes into the second half, when veteran former Spurs striker Dimitar Berbatov struck to make it two.
Alex Oxlade-Chamberlain did pull one back in the 91st minute to give Wenger and Co a glimmer of hope.
But the embarrassment was complete when they were breached yet again a few minutes later, as Yannick Carrasco struck at the death.
Arsenal recovered their poise to win the second leg 2-0, but it wasn’t enough as they crashed out on away goals.
MIDYJYLLAND 2 MANCHESTER UNITED 1 – 2016
Having competed in the Champions League final under Sir Alex Ferguson just five years earlier, those days felt a world away when Louis van Gaal took his patched up side to Denmark in the Europa League in 2016.
A back four featuring the likes of Donald Love and Paddy McNair were given the runaround by their virtually unknown Scandinavian opponents.
Memphis Depay did manage to give them the lead in the 37th minute.
But Pione Sisto pegged them back on the stroke of half time, before Paul Onuachu rounded off an evening to forget for the Red Devils with 13 minutes remaining.
Despite going 1-0 down, United did manage to salvage things at Old Trafford, much in thanks to debutant Marcus Rashford, who stole the show by scoring twice and becoming the new darling of the Stretford End.