Five major upsets in English football before Arsenal’s League Cup shock

How big a shock is the Premier League champions’ 5-3 defeat on penalties after a 1-1 draw with a fourth-tier club?

Arsenal suffered a stunning League Cup fourth-round defeat at fourth-tier Fleetwood Town on Tuesday.

The Premier League champions lost 5-3 on penalties after a 1-1 draw in one of the greatest shocks in the history of English football.

The debate over what is the biggest upset in cup history is never-ending, but here are five other epic cup upsets to rival Arsenal’s humiliation.

Wrexham beat Arsenal 2-1 (1992 FA Cup)

In the previous season, 90 places had separated the two clubs in the English Football League, with Arsenal having claimed their second title in three seasons under manager George Graham.

Alan Smith put the Gunners in front, but Mickey Thomas’s free kick levelled matters with 10 minutes remaining, and Steve Watkin astonishingly claimed a late winner.

Bradford beat Chelsea 4-2 (2015 FA Cup)

Chelsea won the FA Cup five times between 2006 and 2018, but Jose Mourinho’s Blues were humbled by third-tier Bradford at Stamford Bridge.

The Premier League leaders went 2-0 up through Gary Cahill and Ramires.

But Bradford stormed back, and goals from Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates left Chelsea in tatters.

Hereford beat Newcastle 2-1 (1972 FA Cup)

The fourth-round tie that had everything: pitch invasions by Parka-clad fans, and Ronnie Radford scoring one of the FA Cup’s greatest goals.

Malcolm Macdonald put Newcastle ahead eight minutes from time, and it seemed as if there would be no fairytale for the non-league outfit.

But Radford equalised with a screamer from 25 yards, and Ricky George won it for Hereford in extra time.

Wimbledon beat Liverpool 1-0 (1988 FA Cup final)

Wimbledon’s “Crazy Gang” were given no chance to stop Liverpool from claiming a league and cup double in the final at Wembley.

Wimbledon had been a third-tier side four years earlier, and Liverpool had won the title by a margin of nine points.

But Lawrie Sanchez headed home from Dennis Wise’s free kick, before Wimbledon keeper Dave Beasant saved John Aldridge’s penalty to seal the upset.

Grimsby beat Manchester United 12-11 on penalties (2025 League Cup)

United trailed 2-0 as Grimsby duo Charles Vernam and Tyrell Warren scored to expose the flaws in their supposedly superior opponents.

Bryan Mbeumo and Harry Maguire managed to take the second-round tie into extra time.

But Grimsby won on penalties to leave then-United boss Ruben Amorim shell-shocked.