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FA Cup giant killers: Biggest upsets in England’s domestic knockout tournament

England’s FA Cup has a proud reputation as the oldest national club cup competition in world football dating back to the 1871-72 season.

The competition might have seen its prestige take a hit during the Premier League era, but its acclaim with supporters remains as fervent as ever, with the ‘magic of the cup’ never failing to inspire.

The format of the competition allows non-league and lower league clubs the chance to rise through the rounds and take on one of the big boys, despite the odds being stacked against them every season.

The yawning financial gap between the top-flight and the rest of the English football pyramid has made the ladder look unclimbable in league terms, but the FA Cup offers a chance for the mold to be broken and records to be smashed.

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Famous FA Cup giant killers

Ipswich Town 1-2 Maidstone United (FA Cup Fourth Round, 2024)

Non-league Maidstone United produced one of the great cup shocks of recent years when they eliminated Championship promotion-hopefuls Ipswich Town in the fourth round.

The team from the National League North scored two excellent counter-attacking goals — their only shots of the match — and relied on some excellent goalkeeping from Lucas Covolan to help keep Ipswich’s 38 attempts at bay and become the first team from England’s sixth tier to reach the fifth round in 20 years.

Manchester City 0, Wigan Athletic 1 (FA Cup Final, 2013)

Wigan’s win over Manchester City will live long in the memory of Latics fans, as Ben Watson’s added time header achieved the improbable for Roberto Martinez’s underdogs.

The result reflected a rally against City’s growing financial muscle, with Wigan holding the record as the only team to beat City (post-2008), in a major final, prior to their 2021 Champions League final loss to Chelsea.

Liverpool 0, Wimbledon 1 (FA Cup Final, 1988)

Despite the presence of two top-flight teams in the final, the gulf between Liverpool and Wimbledon on and off the pitch, was the key narrative surrounding the ’88 final. 

The ‘Culture Club’ of Kenny Dalglish’s Liverpool against the ‘Crazy Gang’ ended in a shock defeat for the imperious Reds as The Dons upset the odds in typically robust fashion at Wembley.

Wrexham 2, Arsenal 1 (FA Cup Third Round, 1992)

A result that causes a shiver down the spine of Arsenal fans from across generations at any mention of their inglorious night in North Wales is deep-rooted. 

George Graham’s Gunners were the defending First Division champions, against Fourth Division also-rans Wrexham, but a jaw-dropping, Mickey Thomas-inspired late rally caused a pitch invasion, as the hosts took down a genuine giant.

Hereford United 2, Newcastle United 1 (FA Cup Third Round replay, 1972)

Hereford’s win over Newcastle is an age-old trivia question for FA Cup anoraks as they hold the record for the lowest-ranked non-league side to beat a top-flight opposition in English football history. 

Newcastle were given a warning after drawing 2-2 at St. James’ Park, with Magpies star Malcolm Macdonald rumored to have tipped himself to score 10 goals in the replay.

But, Hereford again flipped the script, as Ronnie Radford’s iconic thunderbolt set the Southern Division side on course for an incredible 2-1 win.

Leicester City 1, Wycombe Wanderers 2 (FA Cup Quarter Finals, 2001)

Wycombe’s upset at Leicester was initially focused on their deepest run in the competition, under the guidance of Lawrie Sanchez, who famously netted the Wimbledon winner in 1988.

However, the game will forever be remembered for the name Roy Essandoh.

Belfast-born and Ghanaian-raised Essandoh had an eclectic CV prior to arriving at Wycombe, with spells in Austria and Finland, before an odd turn of events saw his agent respond to a bizarre Ceefax advert from Sanchez looking for a striker, and the stage was set for the journeyman to net a bonkers winner at Filbert Street.

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Last FA Cup winner from lower divisions

The FA Cup has become the reserve of the top Premier League sides in recent seasons with one of Manchester City, Manchester United, Chelsea or Arsenal winning 11 of the last 13 finals.

Wigan’s win over City in 2013 was the last genuine final upset, as Martinez’s side were relegated from the Premier League later that season, despite their Wembley glory.

Cardiff City are the last side outside of the top-flight to reach the final, as the Welsh giants lost out to Portsmouth in the 2010 showpiece.

However, the last team to win the FA Cup from outside of the top tier predates the Premier League, with Trevor Brooking’s famous goal clinching the 1980 trophy, for Second Division West Ham against holders Arsenal.

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