Manchester Utd's Most Embarrassing League Cup Moments

Manchester United have a rich tradition of success in the League Cup, having won it three times since the turn of the millennium and four times overall. 

However, the Red Devils' success in the contest is also framed by sporadic humiliation.

As Louis Van Gaal's men prepare for their fourth-round clash with Middlesbrough on Wednesday, here are the moments when United have been dumped out of the competition in embarrassing fashion...

Manchester United 1-2 Watford, October 1978

United's history of League Cup faux pas takes us all the way back to the 1970s.

In October 1978—a few seasons after George Best, Denis Law and Bobby Charlton had departed the club—they went a goal up over third-tier Watford at Old Trafford in the third round. 

However, a Luther Blissett brace earned the Hornets a famous victory—and a stepping stone in a campaign that went all the way to a semi-final defeat to eventual winners Nottingham Forest.

York City 4-3 Manchester United (agg.), October 1995

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A wise man named Alan Hansen once said: "You'll never win anything with kids."

The former Liverpool star might have been on to something when he saw a United side featuring the youthful influence of Paul Scholes, David Beckham, Phil Neville and Ryan Giggs ship three unanswered goals when struggling Second Division side York City came to town in October 1995. 

A 3-1 win for United in the second leg wasn't enough to turn around the shocking turn of events at Old Trafford. But, as Hansen is well aware, several of the kids involved went on to win a league and FA Cup double that season.

Ipswich 2-0 Manchester United, October 1997

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In 1997-98, United were very much in the midst of their late-90s pomp. However, that season they didn't win a sausage.

The tone of the campaign might have been set by a 2-0 League Cup defeat at Portman Road in October, which saw second-tier Ipswich's ascension to the fourth round confirmed by a Mauricio Taricco long-ranger. 

Ipswich were knocked out in the fourth round by Oxford United. 

Southend 1-0 Manchester United, November 2006

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When Manchester United came to Roots Hall for the League Cup fourth round in November 2006 with a team featuring 11 internationals—including Cristiano Ronaldo and Wayne Rooney—no one expected a struggling Championship side to put up a decent fight.

But Southend, who were eventually relegated to the third tier that season, took the lead through a lovely free-kick that sunk the visitors.

In the following round, the plucky Shrimpers took Tottenham deep into extra time before succumbing to a Jermain Defoe strike. 

Manchester United 0-2 Coventry, September 2007

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In 2007-08, Coventry City were circling round the financial plughole, struggling to survive in the Championship and facing a transfer ban.

Despite this, the Sky Blues headed to Old Trafford for a League Cup third-round tie with a United side featuring six full internationals in the starting XI.

The 11,000 fans who made the journey from the Midlands were treated to a spectacular display and a 2-0 win, which rocked a side who had crashed out to Southend the previous season.

West Ham 4-0 Manchester United, November 2010

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A win over West Ham in the fifth round in 2010-11 would have put United on course to win a third successive League Cup—a feat that has only ever been matched by Liverpool.

However, West Ham abruptly ended that dream with a rousing 4-0 win in the snow at Upton Park.

The star of the show was Nigerian forward Victor Obinna, who assisted all four goals. He now plays in the German second tier with MSV Duisburg.

MK Dons 4-0 Manchester United, August 2014

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Louis Van Gaal's first taste of the League Cup was not a pleasant one, as the Red Devils were handed a humiliating defeat by League One franchise Milton Keynes Dons.

Thanks to their underwhelming league finish the previous season, United found themselves in the second round of the competition for the first time in 19 years.

They failed to register a shot on target until the 72nd minute, at which point the team—featuring the likes of Danny Welbeck, Javier Hernandez and Shinji Kagawa—were already 3-0 down. 

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