Manchester United suffered a humiliating League Cup defeat to League Two Grimsby to end their 2025/26 League Cup campaign before it even began.
United lost 12-11 on penalties after fighting back from 2-0 down to draw 2-2 at the end of 90 minutes at Blundell Park.
That got us thinking, ‘What are the biggest upsets in the history of English domestic cups?’. So we decided here at BOYLE Sports to take a trip down memory lane and put together for you a list of the 5 biggest shocks in English domestic cup history.
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The 5 Biggest Upsets In English Domestic Cup History
Grimsby vs Man United
Grimsby 2 Manchester United 2 (Grimsby won 12-11 on penalties – League Cup, 2025)
United trailed 2-0 after half an hour as Charles Vernam and Tyrell Warren punished haphazard defending and dreadful goalkeeping from Andre Onana.
Substitute Bryan Mbeumo and Harry Maguire, powering home an 89th-minute header, managed to take the second-round tie into extra time.
But Grimsby won on penalties to progress and leave the faces of United players as red as their shirts.
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Chelsea vs Bradford
Chelsea 2 Bradford 4 (FA Cup, 2015)
Chelsea won the FA Cup five times between 2006 and 2018 but Jose Mourinho’s Blues were humbled by League One Bradford at Stamford Bridge.
The Premier League leaders went 2-0 up through Gary Cahill and Ramires and appeared to have one foot in the fifth round.
But Bradford stormed back and goals from Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates dumped Chelsea out.
Wrexham vs Arsenal
Wrexham 2 Arsenal 1 (FA Cup, 1992)
It looked like one of the biggest mismatches when Wrexham were drawn against Arsenal in the third round of the FA Cup.
In the previous campaign, 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’ thumping free-kick levelled matters with 10 minutes remaining, and Steve Watkin astonishingly claimed a late winner.
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Liverpool vs Wimbledon
Liverpool 0 Wimbledon 1 (FA Cup, 1988)
‘The Crazy Gang’ were given no chance to stop Liverpool from claiming a league and cup double 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 Dave Beasant saved John Aldridge’s penalty to become the first goalkeeper to stop a spot-kick in a cup final and Lawrie Sanchez also wrote his name into football folklore by heading home Dennis Wise’s free-kick.
Hereford vs Newcastle
Hereford 2 Newcastle 1 (FA Cup, 1972)
The fourth-round tie that had everything: pitch invasions by Parka-clad fans, John Motson launching his commentary career, and Ronnie Radford scoring one of the FA Cup’s greatest FA Cup goals.
Malcolm Macdonald put Newcastle ahead eight minutes from time and it seemed as if there would be no fairytale for the Southern Football League outfit.
But Radford equalised with a screamer from 25 yards – three minutes later – before Ricky George won it for Hereford in extra-time.
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