Arsenal's League Cup Exit at Fleetwood Joins List of Great English Football Upsets

Arsenal were knocked out of the League Cup in the fourth round by fourth-tier Fleetwood Town on Tuesday, in a result that ranks among the biggest shocks English football has seen. The Premier League champions drew 1-1 and then lost 5-3 on penalties.

Which result counts as the greatest cup upset is a question fans have argued over for decades. Here are five other famous giant-killings that can stand alongside Arsenal's defeat.

In the 1992 FA Cup, Wrexham beat Arsenal 2-1. The previous season, 90 places had separated the two clubs in the English Football League, and Arsenal had just won their second title in three seasons under manager George Graham. Alan Smith put the Gunners ahead, but Mickey Thomas levelled with a free kick 10 minutes from time. Steve Watkin then scored a stunning late winner.

In 2015, third-tier Bradford beat Chelsea 4-2 in the FA Cup at Stamford Bridge. Chelsea won the competition five times between 2006 and 2018, yet Jose Mourinho's side were humbled. The Premier League leaders went 2-0 up through Gary Cahill and Ramires, but Bradford came storming back. Goals from Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates left Chelsea in tatters.

The 1972 FA Cup fourth-round tie between Hereford and Newcastle had pitch invasions by Parka-clad fans and one of the competition's greatest goals. Malcolm Macdonald put Newcastle ahead eight minutes from time, and it looked as though the non-league side would have no fairytale. Ronnie Radford then equalised with a screamer from 25 yards, and Ricky George won it for Hereford in extra time, making it 2-1.

Wimbledon's "Crazy Gang" were given no chance in the 1988 FA Cup final at Wembley, where Liverpool were chasing a league and cup double. Wimbledon had been a third-tier side four years earlier, and Liverpool had taken the title by nine points. Lawrie Sanchez headed in from a Dennis Wise free kick, and Wimbledon goalkeeper Dave Beasant saved a penalty from John Aldridge to secure a 1-0 win.

The most recent of the five came in the 2025 League Cup, when Grimsby beat Manchester United 12-11 on penalties in the second round. United trailed 2-0 after goals from Grimsby duo Charles Vernam and Tyrell Warren exposed flaws in their supposedly superior opponents. Bryan Mbeumo and Harry Maguire took the tie into extra time, but Grimsby prevailed in the shootout and left then-United boss Ruben Amorim shell-shocked.