N.B. This list was compiled taking into account a number of factors, including significance of the occasion, ineptitude of the performance, standard of the opposition and greater ramifications of the outcome.
1. Chelsea 2-2 PSG (2014-15)
GIVEN THE CIRCUMSTANCES, this was an especially poor result from a Chelsea perspective. Comfortably the best team in England at the time, you would expect a Jose Mourinho side to finish off a 10-man PSG team without their best player for much of the match at Stamford Bridge. However, despite their disadvantage, the French side improbably controlled the game and secured their passage to the next stage at the Londoners’ expense.
2. IFK Goteborg 3-1 Man United (1994-95)
As impressive as the famous mid-90s double-winning Man United team were, Europe was the one stage where success eluded them. This 3-1 defeat by Swedish team IFK Goteborg epitomised their woe in the Champions League during this era.
3. Spartak Moscow 3-0 Blackburn (1995-96)
After winning the Premier League in the 1994-95 season, Blackburn’s follow-up season was a big disappointment by comparison. In Europe in particular, Rovers struggled. This 3-1 loss to Spartak Moscow summed up their problems and was also marred by an on-field fight between Graeme Le Saux and David Batty.
4. Arsenal 3-3 Anderlecht (2014-15)
There’s plenty of options to choose from in terms of Arsenal’s European lows from down through the years. This 3-3 draw with Anderlecht ultimately had little impact on their chances of progression but it served as a concise illustration of so many people’s frustrations with Wenger’s men in microcosm, as they played some nice football to go 3-0 up, before letting the lead slip in the way only the Gunners can. It technically didn’t kill their Champions League chances by any means, but it surely had a psychological cost.
5. Real Madrid 3-1 Man United (2002-03)
Not many Champions League matches prompt a manager to re-think his entire philosophy, but that’s what Alex Ferguson did after Man United were well beaten in the first leg of their 2003 Champions League quarter-final against Zidane and co.
6. Liverpool 1-1 Basel (2014-15)
Last season was hugely disappointing for Liverpool, with the Champions League in particular highlighting the many flaws of Brendan Rodgers’ side. Despite a number of inept performances, the Reds still had a chance of reaching the knockout stages in their last group match, but a tame display at home to Basel ensured they would have to settle for a place in the Europa League.
7. Ajax 3-1 Man City (2012-13)
City have been largely flattering to deceive in Europe for years now, however this 3-1 defeat in only their second-ever Champions League campaign may just be their worst performance to date, as they were outclassed by an Ajax side who had nowhere near their level of resources.
