Grimsby beating Man Utd joins the ranks of the biggest cup upsets 🏆⚡️

 

Manchester United’s penalty shootout defeat to League Two Grimsby was a jaw-dropper. But they’re not the first giants to be slayed in domestic cups. 

Here are 10 of the biggest shocks ⬇️

Hereford 2-1 Newcastle (FA Cup, 1972)

The OG giant-killing. Ronnie Radford’s 30-yard thunderbolt and Ricky George’s extra-time goal knocked Newcastle out amid iconic pitch invasions.

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Sutton 2-1 Coventry (FA Cup, 1989)

Non-league Sutton stunned 1987 Cup winners Coventry. Part-timer Matthew Hanlan volleyed in the famous winner.

Wrexham 2-1 Arsenal (FA Cup, 1992)

Arsenal were reigning champions. Wrexham were bottom of the third tier. A thunderbolt free-kick from Mickey Thomas and a late Watkin goal made history.

Man Utd 0-3 York City (League Cup, 1995)

Even Ferguson wasn’t immune. York stunned a United side featuring Giggs, Beckham & co. Paul Barnes’ brace sent the Minstermen through.

See also: What next for Man Utd and Amorim after humiliation at Grimsby?

Liverpool 2-2 Northampton (2-4 pens, League Cup, 2010)

Anfield silenced. League Two Northampton edged Liverpool on penalties after a battling display and late extra-time drama.

Bradford 1-1 Arsenal (3-2 pens, League Cup, 2012)

Fourth-tier Bradford eliminated Wenger’s Arsenal on penalties in the quarter-finals. Vermaelen equalised late, then missed the decisive spot-kick.

Oldham 3-2 Liverpool (FA Cup, 2013)

Luis Suárez couldn’t save Liverpool. Two goals from Matt Smith and a brave Oldham performance toppled the Reds at Boundary Park.

Chelsea 2-4 Bradford (FA Cup, 2015)

Chelsea led 2-0 at Stamford Bridge. The League One Bantams stormed back with four unanswered goals to stun Mourinho’s title-chasing side.

Plymouth 1-0 Liverpool (FA Cup, 2025)

Arne Slot rotated heavily, but Plymouth didn’t care. Ryan Hardie’s penalty was enough to dump out the Reds, who would later go on to lift the Premier League title.

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Grimsby 2-2 Man Utd (12-11 pens, League Cup, 2025)

League Two Grimsby knocked out Premier League giants Man Utd in a marathon shootout. Clarke Oduor held his nerve, Bryan Mbeumo hit the bar, and the Mariners made history.

Cup football. Where dreams live, and giants fall.

Which upset tops your list? 👀