Arsenal suffered one of the most remarkable setbacks in English football history on Tuesday, dropping out of the League Cup fourth round after a 5-3 penalty shootout loss to fourth-tier Fleetwood Town following a 1-1 draw. While debates over the absolute greatest cup upsets are endless, several classic matches stand alongside the Premier League champions’ elimination. 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.
Arsenal are no strangers to monumental cup shocks.
In the 1992 FA Cup, Wrexham famously defeated the Gunners 2-1. Entering that match, 90 places had separated the two clubs in the English Football League the previous season, during which George Graham had guided Arsenal to their second league title in three years. Alan Smith opened the scoring for the visitors, but a Mickey Thomas free kick drew Wrexham level with 10 minutes left before Steve Watkin struck a dramatic late winner.
Another notable upset came in the 2015 FA Cup when third-tier Bradford City stunned Chelsea 4-2 at Stamford Bridge. Although Jose Mourinho’s Blues were dominant in that era, winning five FA Cups between 2006 and 2018, they collapsed after taking an initial 2-0 lead through Gary Cahill and Ramires. Bradford mounted a relentless comeback with goals from Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates.
The 1972 FA Cup produced an iconic fourth-round tie when non-league Hereford United defeated Newcastle United 2-1. Newcastle appeared to secure passage when Malcolm Macdonald scored eight minutes before full-time. However, Ronnie Radford forced extra time with a celebrated 25-yard equalizer before Ricky George sealed the miraculous victory, sparking massive pitch invasions by parka-clad supporters.
In the 1988 FA Cup final, Wimbledon’s “Crazy Gang” halted Liverpool’s bid for a league and cup double with a 1-0 win at Wembley. Wimbledon had been playing in the third division just four years earlier, while Liverpool had swept the league title by nine points. Lawrie Sanchez headed in the decisive goal from a Dennis Wise free kick, and goalkeeper Dave Beasant made history by saving a John Aldridge penalty.
More recently in the 2025 League Cup, Grimsby Town eliminated Manchester United 12-11 on penalties following a second-round thriller. Grimsby took an early 2-0 lead behind goals from Charles Vernam and Tyrell Warren. Although Bryan Mbeumo and Harry Maguire fought back to push the game past regulation, Grimsby ultimately prevailed in the shootout to leave United manager Ruben Amorim stunned. United trailed 2-0 as Grimsby duo Charles Vernam and Tyrell Warren scored to expose the flaws in their supposedly superior opponents.
