
Manchester United’s Old Trafford home - Source: Unsplash
Manchester United fell to arguably the lowest point of the post-Sir Alex Ferguson era as they were shockingly beaten by Grimsby Town in the second round of the Carabao Cup. The Red Devils were already reeling heading into the clash, with their shocking 15th-place finish in the Premier League last season and their failure to win either of their first two games of the new campaign ramping up the pressure on manager Ruben Amorim. However, this shocking defeat to the Mariners has seen the once-great club fall to a new low.
Amorim fielded a strong starting lineup for his side's trip to Blundell Park, with £150m worth of new signings starting up front in the form of Benjamin Sesko and Matheus Cunha. Alongside them, regular first-teamers Amad Diallo, Patrick Dorgu, Manuel Ugarte, Kobbie Mainoo, Diogo Dalot, Harry Maguire, and the much-maligned Andre Onana all started. Even so, it wasn't enough to stop United from slumping.
Manchester United Slump to a New Low
Two goals in eight minutes from Charlex Vernam and Tyrell Warren gave the League Two side a surprising 2-0 lead after just half an hour. Amorim rang the changes at half-time, introducing captain Bruno Fernandes, new signing Bryan Mbuemo, and powerhouse defender Mathijs de Ligt, and ultimately, the adjustments paid dividends. Mbuemo cut the deficit to one with his first goal for his new club on 75 minutes, before Harry Maguire's last-gasp equalizer forced a penalty shootout.
There, it looked as though United would scrape through, with Onana's save from Clarke Oduor providing Cunha with the opportunity to win it. Instead, his spot kick was saved. Grimsby would score their next penalties, and United kept the pace with them until Mbuemo took his side's 13th. The Cameroonian struck the crossbar, handing the Mariners a famous win and arguably Manchester United's most embarrassing defeat for a generation.
Sports betting websites already thought United were in for a painful season. One can bet on sports at Bovada, and the latest odds from the betting giant have the Red Devils listed as a 4/1 outsider to finish in the top four. They were a 22/1 shot to win the title at the start of the campaign, but following a poor start, those odds are now way out at 40/1, and folks looking to bet on sports don’t seem optimistic about their chances.
But as painful as this night was for Manchester United, they aren't the only 'Big Six' club to have suffered a disastrous defeat to fourth-tier opposition. Here are the last three times that happened.
Colchester Stun Pochettino's Spurs
Back in 2019, Tottenham Hotspur were supposed to be a club on the rise. They had just reached the UEFA Champions League final for the first time, and although that ended in defeat, Mauricio Pochettino's fine tenure was leading the North London club back to the upper echelons of the Premier League table. In the fourth round of the 2018/19 League Cup, a trip to fourth-tier Colchester United wasn't supposed to pose much of a threat.
Poch started the likes of Eric Dier, Davinson Sanchez, Dele Alli, and Lucas Moura, before adding Son Heung-min and Christian Eriksen from the bench. Shockingly, though, Spurs weren't able to force a breakthrough, and the tie would eventually head to a penalty shootout after a goalless draw. There, Eriksen saw his spotkick saved by opposition goalkeeper Dean Gerken before Moura smashed a decisive penalty against the crossbar to hand the Essex club - the lowest-ranked team remaining in the competition - one of their greatest ever nights.
Bradford Beat Arsenal to Secure a Semifinal Berth
Seven years earlier, Arsenal were on the hunt for their first piece of silverware in eight years. The Gunners were the sole 'Big Six' club remaining in the League Cup at the quarterfinal stage, and they headed to fourth-tier Bradford City as huge favorites to punch their ticket to the semifinals. Arsene Wenger led with his strongest team, with the likes of Santi Cazorla, Jack Wilshere, and Aaron Ramsey all starting in West Yorkshire.
However, a raucous Valley Parade crowd would prove to be the Gunners' undoing. Bantams winger Garry Thompson volleyed the hosts in front, much to the delight of the sold-out home faithful, and it looked as though that would be enough to secure the win. Then, two minutes from time, captain Thomas Vermaelen nodded home from a Cazorla corner to force extra time and eventually penalties. There, Vermaelen would go from hero to zero, missing the decisive spotkick and sending Bradford through to the semifinals.
Roy Hodgson's Liverpool Beaten By Northampton
In 2010, Liverpool were a million miles away from the force they are in 2025. Roy Hodgson had just taken over from Rafa Benitez, but the future England manager looked woefully out of his depth. They welcomed lowly Northampton Town to Anfield in the third round of the League Cup, and Hodgson rested a number of his top stars with a trip to Manchester United looming days later.
Steven Gerrard and Fernando Torres were nowhere to be found, but some senior players did start, with the likes of Daniel Agger, Ryan Babel, and Lucas Leiva leading the charge. Serbian winger Milan Jovanovic gave the Reds an early lead, but the Cobblers struck back just before the hour mark through Billy McKay to force extra time. There, the League Two side deservedly took the lead through Michael Jacobs and thought they had pulled off the impossible, only for David Ngog to equalize four minutes before the end of extra time.
A 2-2 draw took the contest to penalties, and Liverpool striker Nathan Ecclestone's miss proved crucial. That provided Abdul Osman with the opportunity to send his side through, and he duly obliged, coolly slotting past Brad Jones to claim victory.



