Fleetwood Town Eliminates Arsenal From League Cup

Arsenal’s campaign in the League Cup ended abruptly on Tuesday.

The Premier League champions were eliminated in the fourth round by Fleetwood Town, a fourth-tier club. The match finished 1-1 after regulation, and Fleetwood won the subsequent penalty shootout 5-3.

The result places this defeat in a category of rare shocks in English football history. Fans have long debated which cup upsets rank highest, but five other results stand out for their improbability.

In the 1992 FA Cup, Wrexham defeated Arsenal 2-1. At the time, 90 league positions separated the two clubs. Alan Smith gave Arsenal the lead, but Mickey Thomas equalized with a free kick in the 80th minute. Steve Watkin scored the late winner.

Bradford City, then in the third tier, beat Chelsea 4-2 at Stamford Bridge in 2015. Chelsea had won the FA Cup five times between 2006 and 2018, but Jose Mourinho’s team conceded four goals after Gary Cahill and Ramires put them ahead. Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates scored for Bradford.

Hereford United, a non-league side, defeated Newcastle United 2-1 in the 1972 FA Cup fourth round. Malcolm Macdonald put Newcastle ahead in the 82nd minute, but Ronnie Radford equalized from 25 yards. Ricky George scored the extra-time winner as fans invaded the pitch.

Wimbledon, known as the Crazy Gang, won the 1988 FA Cup final against Liverpool. Liverpool had won the league title by nine points, but Lawrie Sanchez headed in a Dennis Wise free kick. Dave Beasant saved John Aldridge’s penalty to seal a 1-0 victory.

The most recent comparable upset occurred in the 2025 League Cup, when Grimsby Town defeated Manchester United 12-11 on penalties. Grimsby led 2-0 after goals from Charles Vernam and Tyrell Warren. Bryan Mbeumo and Harry Maguire kept United in the game until the shootout, where Grimsby prevailed against Ruben Amorim’s team.