Southend, MK Dons and Coventry: Man United’s biggest Cup upsets

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Manchester United don’t always have it their own way in the League Cup.

In the last 10 seasons, the Red Devils have succumbed to lower league opposition on four occasions.

Jose Mourinho is set to make significant changes for the visit of Burton Albion this week.

Could the Brewers cause another almighty upset?

We take a look at United’s five most shocking League Cup defeats from the last 10 seasons…

Southend United 1-0 Manchester United, 2006-07

Chances are Cristiano Ronaldo and Wayne Rooney had never even been to Southend before this clash at Roots Hall.

We reckon they’ve probably not been back since.

Sir Alex Ferguson was left with jelly and ice-cream all over his face as United went home with their tail between their legs.

The Shrimpers edged ahead in the first-half courtesy of Freddy Eastwood’s stunning 30-yard free-kick.

And amazingly they held on.

Home goalkeeper Darryl Flahavan produced a string of stunning saves to deny the visitors as the Championship side recorded a famous victory.

Manchester United 0-2 Coventry City, 2007-08

“You don’t win anything with kids”, Alan Hansen once proclaimed.

He was certainly right in this instance as United crashed out at home to Coventry City.

Maltese striker Michael Mifsud was the star of the show.

The 5ft 4in forward scored in either half to the delight of the 11,000 travelling supporters.

For United, Dong Fangzhou and Lee Martin (remember them?) would not play another domestic game for the club.

West Ham 4-0 Manchester United, 2010-11

If Bebe, Gabriel Obertan and Federico Macheda are the answer, you have to wonder what the question is.

Here, the Red Devils had no response as they surrendered their unbeaten record in the East End snow.

Former Old Trafford prospect Jonathan Spector haunted the United defence in a hugely one-sided encounter.

West Ham took the lead early on through Spector before the American added another just before half-time.

Carlton Cole helped himself to a brace after half-time as the Hammers put United to the sword.

Manchester United 1-2 Crystal Palace, 2011-12

Palace may be struggling for goals at the moment, but at Old Trafford in 2011 they had no such problems.

So much so in-fact, that Darren Ambrose walloped one in from 35-yards to give the Eagles the lead.

Macheda replied for the hosts as the game went into extra time.

Palace remained in control and went ahead again through Glenn Murray on 98 minutes.

Sir Alex Ferguson’s side had no reply this time as a side containing 10 internationals, including Dimitar Berbatov, exited the competition at the quarter-final stage.

MK Dons 4-0 Manchester United, 2014-15

Perhaps the defining result of the post-Ferguson era.

Louis van Gaal trusted the kids. And the kids let him down.

The Red Devils limped to a hugely embarrassing defeat to the League One Dons, with Benik Afobe and Will Grigg scoring two apiece.

United didn’t register a shot on target until the 72nd minute.

Of the 11 players that started at Stadium: MK on that fateful evening in 2014, only David de Gea remains at Old Trafford.

Click here for all our Manchester United v Burton Albion odds.

All Odds and Markets are correct as of the date of publishing

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Nick Murphy

Nick is a graduate of the University of East Anglia where he doubled up as the sports editor of the student newspaper Concrete. He also supports Dagenham & Redbridge and previously edited the matchday programme at Victoria Road. Other passions include darts, cricket, speedway and horse racing.