Fleetwood's 5-3 Penalty Win Over Arsenal Marks Rarest Cup Upset

English football history is defined by moments when lower-league teams dismantle elite opponents. On Tuesday, the list of such events grew longer when Fleetwood Town, a fourth-tier club, defeated Premier League champions Arsenal.

The match ended in a 1-1 draw during regular and extra time. Fleetwood then converted five penalties to three to secure the victory in the fourth round of the League Cup.

This result sits alongside other famous giant-killings that have defined the sport. In the 1992 FA Cup, Wrexham defeated Arsenal 2-1. At the time, the two clubs were separated by 90 places in the English Football League. Manager George Graham led Arsenal to the title, but Mickey Thomas and Steve Watkin scored for Wrexham to force the shock win.

Chelsea fell to Bradford City in 2015. The third-tier side beat the Premier League leaders 4-2 at Stamford Bridge. Despite goals from Gary Cahill and Ramires giving Chelsea a 2-0 lead, Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates scored four unanswered goals for Bradford under Jose Mourinho's watch.

Hereford United achieved a similar feat in 1972. The non-league side beat Newcastle United 2-1 in the FA Cup fourth round. Ronnie Radford equalized with a shot from 25 yards after Malcolm Macdonald put Newcastle ahead. Ricky George scored the winner in extra time for Hereford, a club that had not yet reached the professional leagues.

Wimbledon's 1988 FA Cup final victory over Liverpool stands out for the context of their rise. Wimbledon had been in the third tier just four years prior. They beat Liverpool 1-0, with Lawrie Sanchez scoring the only goal. Liverpool had won the league title by nine points that season, seeking a double.

The most recent comparable upset occurred in the 2025 League Cup. Grimsby Town defeated Manchester United 12-11 on penalties in the second round. United trailed 2-0 after goals from Charles Vernam and Tyrell Warren. Bryan Mbeumo and Harry Maguire kept United alive until the shootout, where Grimsby prevailed to stun manager Ruben Amorim.