1) 0-4 v Barcelona, Champions League group stage, 1994-95

The night Alex Ferguson realised just how hard it would be to win the European Cup. Johan Cruyff’s Dream Team savaged United, with their World Cup stars Romario and Hristo Stoichkov playing with a brilliance that verged on cruelty. The absence of Peter Schmeichel (because of the foreign-player rule) and Eric Cantona (suspension) was a red herring: United were out of their depth, and eventually went out in the group stage. Those who were part of the burgeoning ABU (Anyone But United) culture loved it.



Manchester United’s malaise goes all the way down to their academy Read more

2) 1-2 v Basel, Champions League group stage, 2011-12

United were used to getting through the group stage on autopilot – until this meek defeat, which meant they were eliminated before the knockout stages for only the second time since the mid-1990s. They were not in a tough group - Benfica, Basel and Otelui Galati - but they drew three of their first give games, which left them in a precarious position even though they were unbeaten. After a 2-2 draw with Benfica, a journalist suggested United were “struggling”, at which point Ferguson decided to find out once and for all whether looks really could kill. Two weeks later United weren’t just struggling, they were out.

3) 0-0 v Galatasaray, Champions League second round, 1993-94

In their first Champions League campaign, United didn’t even make the group stage. They were expected to breeze past Galatasaray in the second round, but few in England realised how fast Turkish football was improving – or how scary their fans were. United were lucky to draw 3-3 in a shambolic first leg at Old Trafford. Then came their ‘Wellcome to the Hell’, as a banner greeting them read, and an impotent 0-0 draw which meant they were out on away goals. After the game Eric Cantona was sent off and United players were assaulted by police in the tunnel.

4) 0-5 v Sporting, Cup Winners Cup quarter-final, 1963-64

A side including the Holy Trinity of George Best, Denis Law and Bobby Charlton went to Lisbon with a 4-1 lead in the Cup Winners’ Cup quarter-final. An apparent formality turned into the harshest of lessons for Matt Busby’s emerging side: Sporting, the eventual winners, routed them 5-0.

5) 1-2 v Midtjylland, Europa League Round of 32, 2015-16

Forget the extreme reaction of social media: this was not the biggest humiliation in Manchester United’s history. Louis van Gaal should not be burned at the stake. Van Gaal’s team have not yet suffered a definitive humiliation to compare with some of the thrashings under Ferguson. But whereas Ferguson’s side tended to have one or two shockers a season and few other low points, Van Gaal’s United have shown exceptional consistency in their accumulation of medium-level embarrassments. Last night was the latest in a troublingly long list.



6) 0-1 v Fenerbahce, Champions League group stage, 1996-97

United had never lost at home in 56 European ties, the sort of record that should by rights be surrendered in an epic duel with one of the great sides. In fact it went with a whimper when they lost 1-0 to Fenerbahce on a subdued night. At the time, it was just another in a series of surreal blows to mark Ferguson’s 10th anniversary: United came into the match after losing consecutive league games 5-0 and 6-3 at Newcastle and Southampton.



7) 0-1 v Zalaegerszeg, Champions League preliminary round, 2002-03

After finishing outside the top two for the first time in the Premier League era, United had to play a European qualifier against a Hungarian side that few could pronounce and even fewer had heard of. They united the ABU nation in mirth by losing to an injury-time goal. Deep down everyone knew United would go through – they won the second leg 5-0 – but that barely reduced the schadenfreude.



8) 0-4 v Porto, Cup Winners Cup second round, 1977-78

A bizarre, self-inflicted embarrassment. United had arranged to play a mid-season exhibition match in Tehran, reportedly part of a deal with the government to end the ban on United playing European matches at Old Trafford. It meant the players were given cholera vaccinations before this vital game in Portugal. Several had a reaction and either missed the match or played at half rat-power. United were trounced 4-0, and a primal 5-2 win back at Old Trafford in the second leg was futile.

9) 0-1 v Lille, Champions League group stage, 2005-06

The game after Roy Keane’s censored MUTV interview was a miserable affair that reinforced Keane’s reported criticisms. United had a midfield of Alan Smith, Kieran Richardson and Darren Fletcher, who bore little resemblance to the world-class midfielder he would become; it felt like the antonym of their great Giggs-Keane-Scholes-Beckham midfield, and defeat to a modest Lille side came as no surprise. United eventually went out in the group stage for the first time in over a decade.

10) 0-1 v Videoton, Uefa Cup, 1984-85

Ron Atkinson’s United were a brilliant cup side – most of the time. They missed a great chance to reach the final of the Uefa Cup, however, when they were beaten by the unknown Hungarian side Videoton on penalties in the quarter-finals. FK Željezničar of Yugoslavia would have been relatively easy semi-final opponents, with Real Madrid waiting for the glamour final that never was.



