The later we get into the FA Cup, the rarer shocks become. The biggest third round upsets are famous, and there’s usually a shock of significance every season. It’s a bit different by the time we reach the fifth round.

Minnows have been knocked out, and the smaller clubs that remain are often drawn against the best clubs in the country.

Teams who have ridden waves of adrenaline and excitement have reached the end of their journey and, in recent years especially, the fifth round has been dominated by Premier League clubs.

The depth of the top sides allows them to see opponents off even with heavily rotated teams.

Featuring three matches from this century and a couple from the distant past, we have selected five of the biggest fifth round shocks in FA Cup history…

Colchester United 3-2 Leeds United (1971)

Fourth tier Colchester were a team of veterans when they hosted Leeds in the fifth round in 1971.

Referred to as ‘Dad’s Army’ by much of the press, they were heavy underdogs against a Leeds team led by Don Revie and featuring Jack Charlton and Norman Hunter.

Ray Crawford was Colchester’s hero at Layer Road, physically imposing himself on a Leeds defence that was vulnerable to the aerial ball. Crawford scored twice in the first half to give the hosts a commanding two-goal lead, and they made it 3-0 just after the interval.

Leeds turned it on after that, though. Two goals in 12 minutes made a comeback look possible, but Colchester clung on for the final few minutes to celebrate what might just be the greatest upset in fifth round history.

Revie congratulated the Colchester players after the match and Crawford became an FA Cup legend.

Burnley 0-1 Lincoln City (2017)

Lincoln’s 2017 FA Cup run was historic. They became the first non-league team in over a century to reach the quarter-finals when they snatched a last-minute victory at Turf Moor against Sean Dyche’s Burnley.

The Imps took over 3,000 to Lancashire for a nervy 90 minutes. Sean Raggett was the hero when he headed past Tom Heaton in the 89th minute, but that didn’t secure the victory the visitors.

Burnley fought straight back, piling on pressure through the five added minutes. Andre Gray could, and perhaps should, have scored an equaliser.

The win made Lincoln only the third non-league team ever to knock out four Football League sides in a single FA Cup run, having already got the better of Oldham, Ipswich and Brighton.

Unfortunately the dream of a Wembley appearance wasn’t to be, as Arsenal thrashed Lincoln 5-0 in the last eight.

Leyton Orient 3-2 Chelsea (1972)

Chelsea featured in our famous fourth round shocks and the west London club crop up again here, albeit several decades before their embarrassing loss to Bradford.

The Blues lifted the FA Cup in 1970 and were heavily fancied to cruise past Leyton Orient, who were near the bottom of Division Two.

A star-studded Chelsea team, featuring Peters Bonetti and Osgood and Ron Harris, arrived at Brisbane Road with few considering anything other than a comfortable win.

The match started how it was expected to, with Chelsea taking a 2-0 lead. Orient didn’t role over, however, and fought back with three unanswered goals to upset their London rivals and head to the last eight.

They were knocked out by another team from the capital in the form of cup holders Arsenal.

Liverpool 1-2 Barnsley (2008)

Liverpool’s FA Cup run was far from straightforward. Ties with Luton and Havant and Waterlooville had become hard work. Despite that, they were obviously expected to get the better of Barnsley at Anfield in the fifth round.

A Champions League clash with Inter a few days later was a bit of a distraction and led to Steven Gerrard and Fernando Torres sitting out.

They still had sufficient quality to win easily though, particularly considering Barnsley had just been forced to sign goalkeeper Luke Steele on an emergency loan.

Dirk Kuyt gave the Reds the lead, but Steele put in the performance of his life to keep it 1-0 at the break.

Stephen Foster equalised before the hour mark and, with Steele holding Liverpool off, Barnsley skipper Brian Howard struck an inch-perfect shot into the bottom corner late on to claim an improbable victory for the visitors.

Arsenal 0-1 Blackburn Rovers (2013)

The 2012/13 season wasn’t a nice one for Arsenal in domestic cup action.

Having been knocked out of the League Cup by Bradford, Arsene Wenger named a very strong team for the visit of Blackburn Rovers. A routine win was surely on the cards at the Emirates.

It was a performance indicative of late-Wenger era Arsenal in many ways. Theo Walcott and Gervinho missed clearcut chances as they failed to break the deadlock against a stubborn defence.

Michael Appleton’s Rovers defended resolutely, and Colin Kazim-Richards delivered the sucker punch in the closing stages.

Arsenal have, of course, gone on to enjoy plenty of FA Cup success since then. Mikel Arteta, who played that day, is now in the dugout. Blackburn remain in the Championship after getting relegated in 2012.

*Credit for the main photo belongs to Matt Dunham / AP Photo*

February 28, 2020
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Sam is a sports tipster, specialising in the Premier League and Champions League.

He covers most sports, including cricket and Formula One. Sam particularly enjoys those on the other side of the Atlantic Ocean – notably MLB and NBA.

Watching, writing and talking about sports betting takes up most of his time, whether that is for a day out at T20 Finals Day or a long night of basketball.

Having been writing for several years, Sam has been working with 888Sport since 2016, contributing multiple articles per week to the blog.

Sam Cox
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No one grew up wanting to be Gary Neville. People will grow up wanting to be Trent Alexander-Arnold or Reece James. The role of the full-back has evolved hugely since the turn of the century.

Full-backs on the best teams are attack-first, defend-later players. A position that was once filled with rejected centre-backs is a home for former wide-midfielders and wingers.

As Southgate selects his England squad for Euro 2020, it is right-back where he has the greatest depth. England’s right-back options are the best in the world with four or five legitimate international quality players, possessing a range of different qualities.

James, Alexander-Arnold, Kyle Walker, Kieran Trippier and Aaron Wan-Bissaka could all be first choice in a different era. Max Aarons is playing his way into that group.

This is where Southgate encounters a dilemma. There is such talent at right-back that it gives England options, but it raises questions too; would it be a waste to leave two or three of the five out of the squad? How can they be used best?

One of the options involves a step backwards, and a change of shape from the 4-3-3 that Southgate has favoured in a strong qualification campaign.

Back Three

This can be considered the moderate tactical change. Southgate did this at the World Cup two summers ago, opting for a back three with Walker as the right-centre-back and using Trippier at wing-back.

Alexander-Arnold would be the wing-back in this scenario, lifting some of the defensive burden which is clearly the weakest area of his game.

Wan-Bissaka is the best candidate for the Walker spot. The Manchester City man is a longshot to make the Euros squad, having been omitted from three successive England squads.

There’s no room for James or Trippier in this team, and neither come close to rivalling Alexander-Arnold as an attacking force down the right flank.

If Southgate rolled with this into the tournament proper, the assumption would be that James or Trippier are taken as cover and they name enough centre-backs to replace Wan-Bissaka if necessary.

Another tweak on the back three option involves a bolder move from Southgate.

Unorthodox

Moving the best right-back in the world to a not-right-back position seems a strange suggestion.

Put your best players in their best positions and build around them is usually a good starting point for any manager. The collection of right-backs at Gareth Southgate’s disposal could, perhaps should, make him test that conventional wisdom.

England have a dearth of midfield options. Dele Alli, James Maddison, Jack Grealish, Alex Oxlade-Chamberlain and Mason Mount are all in contention for an advanced spot, but the deep-lying position is England’s weakest.

Jordan Henderson is a certain starter if fit, but Harry Winks and Declan Rice are uninspiring selections at this juncture.

Given Alexander-Arnold’s distribution, his passing would be invaluable in the centre of the park, as Jamie Carragher has previously suggested for Liverpool.

Alexander-Arnold and Henderson as the central midfield pairing in a 3-4-3 would allow Southgate to use James as the wing-back and potentially Wan-Bissaka as a third centre-back.

It is the most extreme fit-all-the-right-backs-in option, and the least likely since Southgate has not experimented with anything close to this yet and England only have four matches before the group stage starts.

A compromise with Alexander-Arnold and Henderson in a 4-3-3 could be considered, too. With so many very-winnable games in the group, it would have been good to see Southgate try Alexander-Arnold in central midfield.

While the replacements at right-back are weaker, it might just be worth it for the upgrade at England’s clear weak spot.

Alexander-Arnold looked up to Steven Gerrard as a youngster too, “Everything about his game I really admired... I always studied him and wanted to be like him.”

There’s no guarantee he would be Gerrard reincarnate, but he has all the tools to translate into central midfield, even if only on a temporary basis as England look to build on their semi-final run at the World Cup.

Vision for passes few others see, the ability to execute them from both feet and a decent tackler (he’s at 1.6 per game in the Premier League this season, a solid return considering how much possession Liverpool have), Liverpool’s right-back is better on the ball than Henderson, Winks or Rice, and he reads the game well enough to break up play.

He could be a perfect springboard to launch counter-attacks through Raheem Sterling and Jadon Sancho.

As fans prepare for the summer with the Euro 2020 tournament guide, England’s loyal supporters will have many questions – Harry Kane’s fitness, Jordan Pickford’s status, centre-back options – but Alexander-Arnold will not be one of them.

It is a topic that should be at least discussed, and hopefully trialled, between now and England’s tournament opener against Croatia on 14th June.

Most Likely Outcome

With so little time to prepare, the 4-3-3 is set to stay for the Euros with Alexander-Arnold remaining at right-back.

There’s no issue with that, of course, as that shape allows Southgate to use the Sterling-Kane-Sancho front three and possibly fit in two of the advanced midfielders.

Alexander-Arnold in midfield feels like it will be a missed opportunity, however. It might have been a disaster, but it could have delved into England’s greatest strength to address their greatest weakness.

It would leave no room for Alli, Grealish or Maddison without Sancho or Sterling missing out, and that’s an issue.

With injuries possible, England could have benefited from testing different setups in the lead up to the Euros though, and having enjoyed an easy path to qualification, they had ample opportunity to try things.

England are the 5/1 favourites in the latest Euro 2020 odds. They have the best right-back on the planet and Southgate is starting him at right-back.

It’s not exactly a major gripe, but with such a collection of superb talents at right-back, not attempting to use more than one of them in the XI feels like a bit of a waste.

*Credit for the main photo belongs to Alastair Grant / AP Photo*

February 26, 2020
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Sam is a sports tipster, specialising in the Premier League and Champions League.

He covers most sports, including cricket and Formula One. Sam particularly enjoys those on the other side of the Atlantic Ocean – notably MLB and NBA.

Watching, writing and talking about sports betting takes up most of his time, whether that is for a day out at T20 Finals Day or a long night of basketball.

Having been writing for several years, Sam has been working with 888Sport since 2016, contributing multiple articles per week to the blog.

Sam Cox
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