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Kenny Miller won the game for Wolves in a match United dominated.
Manchester United 0, Coventry City 2: 26th September 2007
After a healthy 2-0 win against Chelsea, Sir Alex rotated his squad to give youth a chance. Unfortunately, Nani, Gerard Pique and Anderson fluffed their lines as Coventry City's Michael Mifsud scored an unlikely brace to deny the league leaders progress from the Carling Cup third round.
Benfica 2, Manchester United 1: 26th September 2005
Six years ago and it was again Benfica breaking United hearts in Europe. 2005 would see Sir Alex's side finish bottom of their group and crash out of Europe early on. It was an embarrassingly immature conclusion for a team also struggling domestically. Of course they would go on to lift the Champions League trophy three years later in Moscow against Chelsea, but such glories seemed impossibly remote in the darkest days of 2005.
Wolves 1, Manchester United 0: 17th January 2004
In a match United dominated, a fluke Kenny Miller goal secured the three points for Wolves. For the entire 90 minutes, United could do anything but score a goal leading to one of the most excruciatingly frustrating results in their recent history.
Manchester United 0, Borussia Dortmund 1: 9th April 1997
Emotions ran high in the run up to the club's first ever Champions League semi-final against Borussia Dortmund. Whilst the red half of Manchester geared itself up for glory, Lars Ricken had other ideas, firing home to give the German side an important first leg away win. Cantona was particularly wasteful in front of the opposition goal, squandering a number of chances. United lost the reverse fixture by the same result and were knocked out of the competition.
Manchester United 0, Portsmouth 1: 8th March 2008
By the end of this FA semi-final, Rio Ferdinand would be standing in as goalkeeper after a Tomasz Kuszczak red card. Sulley Muntari converted the ensuing penalty past Ferdinand as Portsmouth crept into past United and into the final.