Grimsby Town Shock Manchester United: Where Does it Rank Amongst the Biggest Ever Cup Upsets?

Grimsby Town Shock Manchester United: Where Does it Rank Amongst the Biggest Ever Cup Upsets?

Wednesday night’s tragic shock was just the latest horror show United fans have experienced over the past decade. It also marked another stamp in their history which fans and shareholders alike will not want to hear. Grimsby Towns' victory meant they had become the first-ever club competing in the fourth tier of English football or lower to knock Manchester United out of a cup competition.

A game in which United almost clutched a second half comeback, despite being 2-0 down, came down to one of the most exciting penalty shootouts we have seen in a while; after 20 minutes, and 26 penalties, it was all over, and the Mariners earned a trip to Sheffield Wednesday in the third round.

This cupset was just the latest, and it is always exciting when a minnow club steps up to cause a shock upon a Premier League giant. In this piece, we explore the top 7 EFL Cup upsets of all-time, and where this latest underdog story ranks amongst them.

LIMSBY TOWN!! 🏆🐟

League Two side Grimsby Town have deservedly knocked out Premier League giants Manchester United 12-11 on penalties following a 2-2 draw at Blundell Park… pic.twitter.com/XA8A9rGQjj

— The92Bible (@The92Bible) August 27, 2025

Liverpool 2-2 Northampton Town (2-4 on Penalties) – 2010

First up on the list is the Cobblers recording an emphatic piece of history at Anfield back in 2010. A side which were then competing in the fourth tier of English football, came to Anfield and knocked out Roy Hodgson’s Liverpool.

Despite there being only one other team from a lower domestic position than the Cobblers that had knocked out Liverpool away from home, after Milan Jovanovic’s opener for the hosts, it seemed like Northampton would be the latest sufferers to the Reds.

However, they never gave up, and a Billy McKay strike sent the tie to extra-time before Michael Jacobs gave the Northants side a surprise lead. David N’Gog sent the game all the way to penalties, where Northampton created a bit of cup magic, advancing to the next round.

10 years ago today, Roy Hodgson’s Liverpool were knocked out of the League Cup by fourth-tier Northampton Town at Anfield - Dark times pic.twitter.com/BRCI9YnEoB

— Anfield Edition | æ (@AnfieldEdition) September 22, 2020

Bradford City 1-1 Arsenal (3-2 on Penalties) – 2012

Next, we feature Bradford City’s iconic scalping of Arsenal to advance to the semi-finals of the League Cup. This Quarter final came during their fairytale run to Wembley in the 2012/13 season, and this result remains one of their most historic wins to this day.

Hosting an Arsenal side featuring the likes of Santi Cazorla, Lukas Podolski, and Gervinho, just reaching this point in the competition already gave the Bantams a substantial financial boost, but what came in the following couple of hours saw thousands of jaws drop to the floor.

An immaculate Garry Thompson volley stunned the away end and sent the home fans into jubilation, giving the hosts a shock lead; one they settled on until the dying moments when a piece of brilliance from Cazorla left an easy header for captain Thomas Vermaelen to restore parity. The game eventually went to spot-kicks, and it was Vermaelen’s missed penalty that sent Arsene Wenger’s Gunners packing.

Bradford 1-1 Arsenal (p)
Capital One Cup 2012/13

Bradford stunned Arsenal in the quarter-finals. Penalties decided it, with Vermaelen’s miss knocking the Gunners out. One of the first huge cupsets of the century. pic.twitter.com/WBYf9iXzlr

— Squawka (@Squawka) August 28, 2025

Grimsby Town 2-2 Manchester United (12-11 on Penalties) – 2025

The most recent cup upset and the main feature in this article. Ruben Amorim’s United had not enjoyed a strong start to the 2025/26 season, recording a loss and a draw in their opening two games. Many thought the visit to Grimsby on Wednesday would prove a stepping stone to push them forward and provide a much needed boost, but they instead experienced a whole new low.

The Mariners found themselves at a miraculous 2-0 lead at half-time thanks to goals from Charles Vernam and Tyrell Warren. They almost entered dreamland just past the hour mark, but Cameron Gardner’s goal was controversially ruled out.

Late goals from summer signing Bryan Mbeumo and a customary clutch Harry Maguire header saw the match head to penalties. But after about 20 minutes and 26 penalties, it was the Mariners who ran out victorious, ensuring United were subject to another week of scathing memes.

Notts County 3-0 Tottenham Hotspur – 1994

In 1994, a Tottenham squad featuring Teddy Sheringham, Jurgen Klinsmann, and a young Sol Campbell travelled to Nottingham to face tier two outfit Notts County.

This County side were relegated to the third tier this same season, but they did at least provide the fans with a moment to remember, after humiliating the Lilywhites 3-0 on the night, thanks to goals from Tony Agana and a Gary McSwegan brace.

The match also saw Ossie Ardiles’ final fixture, as he was sacked by then Chairman Alan Sugar just days after this embarrassing result.

Southend United 1-0 Manchester United – 2006

At third on our list is Southend United’s mammoth shock over Premier League juggernauts Manchester United in 2006. They defeated a Sir Alex Ferguson side featuring the likes of future Ballon d’Or winner Cristiano Ronaldo and Wayne Rooney – and the same squad which also won the Premier League title just six months on.

The evening remains one of the biggest nights in the history of the Shrimps, who created one of the biggest upsets of the 21st century. There was just the one goal scored in the match, by Southend’s Freddy Eastwood as his stunning free-kick sent the holders out of the League Cup.

1️⃣ 0️⃣ | Blues beat @ManUtd 10 years ago today at Roots Hall in the @EFLCup thanks to Freddy Eastwood's free-kick! 🔵⚽ pic.twitter.com/5sRdb7wJUO

— Southend United FC (@SUFCRootsHall) November 7, 2016

Swindon Town 3-1 Arsenal – 1969

This result is potentially the most historic on the list of cup upsets, as Swindon remain the last club to win an English domestic cup from outside of the top two divisions.

A Roger Smart goal gave the Robins a surprise lead, before a late Bobby Gould finish sent the match to extra-time. It was here that a Don Rogers brace sealed what is still one of the biggest cup shocks in history as Swindon lifted their first ever major trophy.

The Robins’ whole cup journey remains a fairytale too, needing a replay to advance in four of the six rounds before the final. At the time of Swindon’s greatest cup success, they were playing in the third tier of England. This trophy also remains their first and only major honour.

Swindon Town will proudly wear a new Carabao Cup sleeve badge, recognising our unforgettable League Cup victory in 1969 ❤️

— Swindon Town Football Club (@Official_STFC) August 12, 2025

Manchester United 0-3 York City – 1995

Finally, we head back in time to 1995, where York City were partaking in the third tier of English football, and were tasked with a trip in the second round to Old Trafford to take on Manchester United.

This game came during the midst of United’s dominance over English football in the ‘90s, and it sent fans all over the country into disbelief when they saw the score.

Playing a Red Devils lineup that featured three young class of ’92 members in Phil Neville, David Beckham, and Ryan Giggs, York City went on to cause one of the biggest cup upsets to this day and arguably the biggest in the League Cup’s history. A brace from Paul Barnes and a goal from Tony Barras inflicted a humiliating 3-0 home defeat to Sir Alex and co at The Theatre of Dreams.

It’s 28 years to the day since Old Trafford witnessed one of the shock results of the 90s.

Manchester Utd 0-3 York City.

Some serious David and Goliath stuff in the Coca-Cola Cup.pic.twitter.com/hL5GHfonBu

— Stu’s Football Flashbacks (@stusfootyflash) September 20, 2023