Manchester United head to League 1 Shrewsbury on Monday night in what is arguably the pick of this weekend’s FA Cup Fifth round action, and history reveals the Premier League giants have reason to be cautious against the underdogs.
Micky Mellon’s Salopians need only look through the annals of history to see United have come unstuck against lower-league opposition before, and with the Reds in the middle of European action and without their skipper Wayne Rooney, is there another Cup upset on the cards?
Red Devils fans may want to look away now, but for the rest of you, we’ve dug up some of United’s most infamous cup exits…
We’ll begin many moons ago with a trip to the south coast…
Bournemouth – 1984
A far cry from the Premier League colleagues they are now, back in 1984 Bournemouth were scrapping under a young Harry Redknapp to stay in the Third Division.
Man United headed to Dean Court for an FA Cup third round tie locked in a title-fight with Liverpool, having already claimed the Charity Shield.
But despite Ron Atkinson fielding a full-strength team, including England star Bryan Robson, Milton Graham and Ian Thompson handed the Cherries arguably their most famous win.
United would beat Barcelona two months later. A true cupset.
York City -1996
While they ended up claiming a League and Cup double, United suffered a shock exit in the League Cup to Division Two strugglers York.
Even more incredible was the 3-0 first-leg victory for the Minstermen at Old Trafford against a team featuring Lee Sharpe, David Beckham, Ryan Giggs and a host of other first-team regulars.
All the big names returned for the second leg – Eric Cantona, Andy Cole, Peter Schmeichel et al – but despite taking an early 2-0 lead at a packed Bootham Crescent, York held on for a famous 4-3 aggregate victory.
Southend – 2007
When United head to Roots Hall for a League Cup third round contest with Southend, they sat atop the Premier League having won 10 of their opening 12 fixtures in all competitions.
Their Championship opponents however, lay rooted at the foot of the table having already lost ten times and conceded 16 goals at home.
Sir Alex Ferguson included Wayne Rooney and Cristiano Ronaldo for the trip to Essex, but both superstars could only take notes as Freddie Eastwood curled a stunning free-kick past Tomasz Kuszczak.
It proved to be the only goal of the game as Rooney and co failed to break down their plucky opponents.
Leeds United – 2010
This one wasn’t just a Cup exit to a lower-league team, it was the most rivalled of all lower-league teams.
United entered 2010 just two points behind Chelsea in the title race, and they’d featured in each of the last two Champions League finals.
Leeds had endured difficult times since their heady days of European football, but were looking to bounce back and had lost just once in League One when they visited Old Trafford.
It wasn’t United’s strongest team, but it still featured Dimitar Berbatov alongside Rooney, but Jermaine Beckford’s first-half goal proved enough as Leeds revelled in ousting their illustrious rivals.
MK Dons – 2014
Louis van Gaal endured quite the wake-up call as United headed to Milton Keynes for a second round League Cup clash.
Having failed to win either of his first two games in charge, Van Gaal led his stuttering side to Buckinghamshire, and endured more of a cup humiliation than a cup upset.
Will Grigg handed the League 1 side the first-half advantage, but United capitulated in the second half as Grigg made it 2-0 before Benik Afobe scored twice to complete a 4-0 rout.
Van Gaal’s side didn’t have a shot on target until the 72nd minute, sound familiar?
We must also doff our caps to Barnsley’s FA Cup success in 1998, while further mentions must go to Cambridge United, Crawley, Exeter and Burton for admirable performances against the Premier League behemoths in recent campaigns.
All Odds and Markets are correct as of the date of publishing.