What Are The Most Famous FA Cup Fifth Round Upsets?

What are the most famous FA Cup fifth round upsets? There have been a number of shock results over the years that live long in the memory. 

Typically, it’s the FA Cup third round upsets that usually generate the biggest headlines. Especially with a huge David downing Goliath outcome.

However, the deeper a team goes into the famous competition, surprise results are more of a rarity. That is perhaps owing to the fact it’s mainly just Premier League sides that remain at that stage.

Since the turn of the century, that really has been the case. Owing to the riches top-flight sides can boast, they are easily able to rotate their starting XI’s and still avoid a banana skin along the way.

However, that isn’t always the case. Three of our five FA Cup fifth round upsets all occurred from 2008 onwards. Scroll down now to have a look at the most famous shock results.

Arsenal 0-1 Blackburn (2012/13)

Blackburn dropped down to the EFL Championship the previous season but reminded Arsenal of their Premier League credentials at the Emirates in February 2013.

On paper, the FA Cup fifth round clash looked like a home banker but Colin Kazim-Richards and his Rovers teammates had other ideas.

The North Londoners peppered the visitors goal all afternoon without finding the breakthrough. It was in the closing stages that Kazim-Richards struck to put Michael Appleton’s side into the quarter-finals.

Interestingly, current Reds boss Mikel Arteta featured that day. It was also the second time that campaign Arsene Wenger’s side had fallen victim to lower-league opposition after Bradford knocked them out of the League Cup.

Leyton Orient 3-2 Chelsea (1971/72)

The Chelsea side of the early seventies was littered with a number of star players. Ron ‘Chopper’ Harris, Peter Osgood and Peter Bonetti all featured in this famous FA Cup fifth round upset at Brisbane Road.

Unsurprisingly, many expected the Blues to march into the quarter-finals without a glitch. However, the magic of the cup showed its prominence on a bitterly cold day in East London.

A bumper crowd of 30,329 squeezed into Leyton Orient’s home ground and the Match of the Day cameras were in attendance as well.

Osgood and Dave Webb gave the West Londoners a comfortable 2-0 lead and that appeared to be that. However. the O’s hit back three times on the muddy pitch through Phil Hoadley, Mickey Bullock and Barrie Fairbrother to seal a famous win.

Colchester 3-2 Leeds (1970/71)

Just a year before Leyton Orient’s exploits, Colchester United produced arguably the greatest FA Cup fifth round upset ever witnessed. The fourth tier side managed to beat Don Revie’s mighty Leeds side.

The Whites side featured players such as 1966 World Cup winner Jack Charlton, Norman Hunter, Billy Bremner and Johnny Giles. Nonetheless, they were no match for the side from north-east Essex.

On a freezing cold afternoon in front of 16,000 ers packed into Layer Road, the U’s took a commanding 3-0 lead over the First Division giants.

Revie’s side did manage to make the scoreline a little bit more respectable but that’s as good as it got for the Yorkshire side. The real hero of the afternoon was Ray Crawford – netting twice for the home side in a David vs Goliath slaying.

Liverpool 1-2 Barnsley (2007/08)

In 2008, Liverpool fell victims to Championship side Barnsley at Anfield. The Tykes had a goalkeeping crisis leading up to the match and drafted in Luke Steele on an emergency loan.

Steele proved to be the bane on the Reds attack as he continuously thwarted the Merseysiders but Dirk Kuyt did manage to get the better of him after 32 minutes.

Into the second period, Steve Foster stunned the home crowd when he equalised. Steele continued to frustrate Rafa Benitez’s side before Brian Howard netted a last-gasp winner.

The away ers went into pure pandemonium and Benitez’s side were left baffled at the outcome. In the quarter-final, Barnsley continued their fairytale as they beat Chelsea 1-0 at Oakwell.

Burnley 0-1 Lincoln (2016/17)

Lincoln City achieved FA Cup immortality when they became the first non-league side in over 100 years to reach the quarter-finals.

Sean Raggett was the hero when he headed home in the dying embers of the game against Premier League side Burnley at Turf Moor in February 2017.

Despite Tom Heaton’s efforts of clawing the ball away, Raggett’s header had clearly crossed the line which sent the 3,210 Imps fans into raptures.

However, the Conference side had to endure an agonising five minutes of injury-time which saw Andre Gray denied by a fine stop from Paul Farman.