Arsenal suffered a major blow in the League Cup fourth round on Tuesday, succumbing to fourth-tier Fleetwood Town. The Premier League champions were eliminated 5-3 in a penalty shootout following a 1-1 draw, marking one of the most stunning results in the history of English football.
While debates over the ultimate cup upset remain endless, the astonishing defeat adds to a long legacy of unexpected domestic knockouts. Five other classic English cup victories highlight how lower-league side defying the odds against heavy favorites. But here are five other epic cup upsets to rival Arsenal’s humiliation, the debate over what is the biggest upset in cup history is never-ending.
In the 1992 FA Cup, Wrexham famously defeated Arsenal 2-1. Just a season earlier, the two teams were separated by 90 league places while George Graham’s Gunners had secured two titles within three years. Alan Smith initially put Arsenal ahead, but Mickey Thomas leveled with a 25-yard free kick before Steve Watkin struck late to finish the turnaround. But Mickey Thomas’s free kick levelled matters with 10 minutes remaining, and Steve Watkin astonishingly claimed a late winner, alan Smith put the Gunners in front.
Another monumental surprise came in 2015 when third-tier Bradford City stunned Chelsea 4-2 at Stamford Bridge in the FA Cup. Jose Mourinho’s Blues, who claimed five FA Cup trophies between 2006 and 2018, took a 2-0 lead through Gary Cahill and Ramires. However, Bradford staged a remarkable comeback with goals from Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates.
Back in 1972, non-league Hereford United defeated top-flight Newcastle United 2-1 in a chaotic fourth-round FA Cup replay remembered for pitch invasions. Malcolm Macdonald handed Newcastle an 82nd-minute lead, but Ronnie Radford produced an iconic 25-yard equalizer before Ricky George secured victory in extra time.
The 1988 FA Cup final produced another historic moment when Wimbledon’s “Crazy Gang” disrupted Liverpool’s quest for a double with a 1-0 win at Wembley. Lawrie Sanchez scored from a Dennis Wise free kick, and Dave Beasant made history as the first goalkeeper to save an FA Cup final penalty, stopping John Aldridge’s spot kick.
More recently, Grimsby Town ousted Manchester United from the 2025 League Cup second round on penalties. After Charles Vernam and Tyrell Warren established a 2-0 lead for Grimsby, late goals from Bryan Mbeumo and Harry Maguire sent the game to extra time, with Grimsby eventually winning 12-11 in a dramatic shootout that left Ruben Amorim defeated. United trailed 2-0 as Grimsby duo Charles Vernam and Tyrell Warren scored to expose the flaws in their supposedly superior opponents.
