Grimsby pulls off a stunning EFL Cup upset, defeating Manchester United in a dramatic match

Manchester United suffered a stunning early exit from the EFL Cup, falling to League Two side Grimsby Town on penalties in a result that will be remembered for years.

United fought back from 2-0 down with just 15 minutes remaining to draw 2-2, but ultimately lost 12-11 in a remarkable shootout. The last time United endured such humiliation in a domestic cup came 30 years ago, when York City famously won 3-0 at Old Trafford.

Following Grimsby’s shock win, Samuel Ofori-Ampaw @net2tv takes a look back at some of the most unforgettable cup upsets in FA Cup and EFL Cup history.

Grimsby 2-2 Man Utd (12-11 pens, EFL Cup, 2025)
A result that stunned English football—not just for the upset itself but the way it unfolded. League Two Grimsby led 2-0 through goals from Charles Vernam and Tyrell Warren after 30 minutes. Bryan Mbeumo pulled one back in the 75th minute before Harry Maguire leveled late on. What followed was a marathon shootout, where both teams saw all 11 players take a penalty. After Clarke Oduor scored for Grimsby, Mbeumo, attempting his second, struck the bar—sending Grimsby through.

Chelsea 2-4 Bradford City (FA Cup, 2015)
League One Bradford, sitting 49 places below Chelsea, overturned a 2-0 deficit at Stamford Bridge. After goals from Gary Cahill and Ramires, Bradford rallied through Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates to shock Jose Mourinho’s title-chasing side.

Oldham 3-2 Liverpool (FA Cup, 2013)
With stars like Suarez, Sterling, and Sturridge in the lineup, Liverpool were heavy favourites. But Oldham, battling financial problems, fought valiantly. Matt Smith scored twice and Reece Wabara added a third. Despite Joe Allen pulling one back and Steven Gerrard’s introduction, the Latics held firm.

Bradford 1-1 Arsenal (3-2 pens, EFL Cup, 2012)
Fourth-tier Bradford reached the League Cup quarter-finals and stunned Arsenal. Garry Thompson put the hosts ahead before Thomas Vermaelen equalised late. In the shootout, Vermaelen missed the decisive penalty, echoing Mbeumo’s miss for United years later. Bradford went on to beat Aston Villa in the semis before losing the final to Swansea.

Liverpool 2-2 Northampton (2-4 pens, EFL Cup, 2010)
Anfield witnessed another shock as League Two Northampton edged out Liverpool on penalties. After goals from Jovanovic, McKay, Jacobs, and Ngog took the game to spot-kicks, Abdul Osman’s calm finish sealed a famous win for the Cobblers.

Man Utd 0-3 York City (EFL Cup, 1995)
Even Sir Alex Ferguson wasn’t immune to League Cup shocks. Despite a strong lineup featuring Beckham, Giggs, and Sharpe, United were dismantled by third-tier York. Paul Barnes struck twice, including a penalty, before Tony Barras added a third. United won the second leg 3-1, but York advanced 4-3 on aggregate.

Wrexham 2-1 Arsenal (FA Cup, 1992)
League strugglers Wrexham, bottom of the Third Division, faced defending champions Arsenal. After Alan Smith put the Gunners ahead, Mickey Thomas equalised with a thunderous free-kick, and Steve Watkin scored the winner minutes later in one of the FA Cup’s most iconic moments.

Sutton 2-1 Coventry (FA Cup, 1989)
Non-league Sutton United pulled off a monumental upset against top-flight Coventry, who had lifted the FA Cup just two years prior. Goals from Tony Rains and Matthew Hanlan saw Sutton claim a place in cup folklore.

These matches remind us why domestic cup competitions remain so compelling—where underdogs dare, and giants can fall. Let us know which upset you think was the greatest.