5 League Cup Shocks Involving Manchester United

Rob Blanchette@@_Rob_BFeatured ColumnistAugust 26, 2014

5 League Cup Shocks Involving Manchester United

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    Jon Super/Associated Press

    Over the course of football history, Manchester United have been one of the traditionally great cup sides in the English game.

    However, they have also been involved in a handful of surprising results in the League Cup.

    The Red Devils travel to MK Dons on Tuesday, with Louis van Gaal needing to avoid a humiliating defeat.

    The domestic cup competitions have not been a priority for United for many years, but with no Champions League football this season, suddenly the Old Trafford club are interested in the League Cup's value and merit once again.

    Here, we take a look at five matches that shocked the watching fanbase.

Southend United v Manchester United

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    In November 2006, Manchester United were the holders of the League Cup.

    Sir Alex Ferguson was celebrating 20 years with United, and a mandatory defence of the title was needed at lowly Southend in order to reach the quarter-finals.

    However, things did not go the team's way when they met unbelievable resistance from the Championship strugglers.

    In the end, it was the Shrimpers who proceeded to the last eight, a Freddy Eastwood thunderbolt from 30 yards winning the match 1-0. 

    United's team was led by Wayne Rooney and Cristiano Ronaldo, but their brilliance was not enough to beat Southend goalkeeper Darryl Flahavan, who was inspirational. 

    The 11,500 fans crammed into Roots Hall enjoyed one of their club's greatest nights in their history. 

Manchester United v Sunderland

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    Jon Super/Associated Press

    It became one of the most farcical nights in Old Trafford history and compounded the misery felt during the David Moyes reign.

    Sunderland came to Manchester with a goal advantage in the League Cup semi-final of 2014-15.

    Despite United's shaky form, confidence was high enough to expect a win and a trip to Wembley.

    However, Moyes' team were crippled by the occasion and failed to hurt Sunderland, as Gus Poyet's men dug in.

    The game went to extra time with United leading 1-0, but a Phil Bardsley speculative effort was spilled by David de Gea into his net, giving the Black Cats the lead in the 119th minute.

    With one last attack, United rescued the match from the jaws of defeat, Chicharito scoring with almost the last kick of the game.

    The tie went to penalties, but United crumbled and fell.

    Sunderland won quite possibly the worst penalty shootout in modern times, prevailing 2-1 as United missed four of their spot-kicks. 

Arsenal v Manchester United

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    United have not always been on the end of a League Cup shock, as the 1990-91 season witnessed.

    The Red Devils travelled to Highbury to navigate their way past a very good Arsenal team who were at the top end of their game.

    Ferguson's United played the match of their lives, dismantling the Gunners and winning 6-2.

    Arsenal had been imperious at home during that period and went on to lift the Division One league championship the following year, only losing one game all season. 

    The match represented the breakthrough of Lee Sharpe, who smashed in a hat-trick on the night.

    It was the start of the Red Devils' era of domination that would run for over two decades. 

Manchester United v York City

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    On paper, it was a mismatch, but York City's trip to Old Trafford in the League Cup of 1995 was to go down in history.

    It was the lower-league team who caused one of the competition's greatest upsets ever. They crushed United, winning the first leg 3-0.

    A brace from Paul Barnes and a goal by Tony Barras sealed the famous win for York. 

    On the night, United fielded a weakened side that featured an array of talent such as David Beckham, Ryan Giggs and Peter Schmeichel.

    Ferguson recalled Eric Cantona for the second leg of the tie. However, despite winning 3-1, United crashed out. 

Manchester United v Sheffield Wednesday

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    In 1991, United were in the ascendancy on their way to beating Barcelona for the European Cup Winners' Cup in Rotterdam.

    They were holders of the FA Cup and on the hunt for trophies like at no point in their recent history.

    United were the overwhelming favourites to beat Second Division team Sheffield Wednesday in the final of the Rumbelows Cup at Wembley but hit a brick wall at the national stadium.

    The Red Devils lost the match 1-0, in what was a crushing blow for Ferguson at the time.

    However, United were to recover well and drive toward their first stage of Premier League dominance.

    They also collected the League Cup the following season, beating Brian Clough's Nottingham Forest in the final.