Manchester United's 10 most embarrassing defeats

#8 Southend United 1 - 0 Manchester United (November 2006)

Manchester United had won the Carling Cup in the 2005-06 season, and were celebrating Sir Alex Ferguson’s 20 years in charge of the club when they faced lowly Southend, a team struggling in the Championship.

However, a brilliant performance on the night against a team that boasted of international stars like Wayne Rooney and Cristiano Ronaldo helped the Championship side beat the champions and eventually progress to the quarterfinals of the competition. They were relegated that season, but Freddy Eastwood’s freekick saw them claim one of the greatest wins in the club’s history.

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