The Gunners had lost just one game so far this season, and fielded a side with familiar names such as Kai Havertz, Victor Gyokeres and World Cup winner Martin Zubimendi, but were eliminated by a team 84 places below them in the football pyramid.
The penalty shootout victory saw goalie Joe Lynch become the hero, before teenage defender Conor Haughey smashed home the winning spot kick to send the Cod Army into delirium and spark a classic pitch invasion.
The victory is being talked about as the greatest upset in the competition’s history, so how does it compare to these memorable giant-killings?
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Southend 1-0 Man Utd (2006)
The Championship strugglers faced a United team that boasted Wayne Rooney and Cristiano Ronaldo in their ranks, and were the holders going into this clash at Roots Hall.
But not one of the 10 internationals Sir Alex Ferguson’s side had on display could make a difference as the Shrimpers struck the decisive blow.
Freddie Eastwood’s 30-yard free-kick was enough to see off a United team that would go on to win the Premier League title that season, and give the Essex side their biggest-ever win.
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Colchester United 0-0 Tottenham Hotspur (4-3 on pens, 2019)
A game that pitted League One Colchester, the lowest-ranked side left in the competition at that point, against a Tottenham side, who earlier that year had competed in the Champions League final.
The result? Well, the likes of Christian Eriksen, Dele Alli and Son Heung-min failed to break down a stubborn United side, and after a goalless draw the game went to penalties.
After misses from Eriksen and Lucas Moura, Tom Lapslie scored the winning spot-kick to book Colchester a place in the last 16 for the first time in over 40 years.
Liverpool 2-2 Northampton (2-4 on pens, 2010)
Roy Hodgson looked like a lonely figure on the rain-drenched touchline as Liverpool suffered one of their most infamous home defeats to League Two Northampton.
Milan Jovanovic had put the Reds ahead, but Billy McKay took the game to extra time, before the sides traded goals again to send the game to a shootout.
Abdul Osman put away the winning penalty to give the Cobblers a famous win on Merseyside.
Bradford City 1-1 Arsenal (3-2 on pens, 2012)
A memorable year for the Bantams as their cup exits took them all the way to a Wembley final in 2013, and it included this victory against the Gunners.
Garry Thompson opened the scoring for the home side, and it took a late equaliser from Thomas Vermaelen to take the game to extra time, and then penalties.
Santi Cazorla and Vermaelen missed their spot-kicks and allowed Bradford to progress to the semi-finals.
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Grimsby 2-2 Man Utd (12-11 on pens, 2025)
A night when things went from bad to worse for Ruben Amorim as his Manchester United were eliminated by a fourth-tier side for the first time in their history, while he became a viral sensation thanks to his tactical board-tweaking in the pouring rain.
Grimsby went 2-0 up in this game thanks to goals from Charles Vernam and Tyrell Warren before the Premier League side did claw things back through Bryan Mbeumo and a late Harry Maguire leveller to take the game to a shootout.
After a mammoth 24-kick spot-kick battle, it was Mbeumo who missed his second penalty to see United sink to new depths against the Mariners.
Man Utd 0-3 York City (1995)
A United team in their mid-90s pomp under Sir Alex Ferguson, that included David Beckham, Lee Sharpe and Ryan Giggs, failed to overcome York City at Old Trafford.
Paul Barnes – father of current Newcastle star Harvey – and a Tony Barras header stunned the home side in the biggest upset of the era.
United pulled out all the stops for the return leg, but despite clawing back the 3-0 deficit, Scott Jordan scored for Alan Little’s men to send them through 4-3 on aggregate.
MK Dons 4-0 Man Utd (2014)
What is it when United and the League Cup? Another exit at the hands of a lower-league side, and one of the most humbling, too.
This was Louis van Gaal’s Red Devils, who went to Stadium MK in the second round and fielded a side that included David De Gea, Javier Hernandez and Jonny Evans.
However, braces from Wigg Grigg and Arsenal loanee Benik Afobe gave the Dons a resounding victory over the Premier League team.
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