Grimsby and Nine Other Times Man Utd Have Suffered Embarrassing Defeats

The latest example came against League Two side Grimsby Town in the EFL Cup, a result that stunned Old Trafford and reminded fans that no team is immune from football’s unpredictability.

But Grimsby are not alone on the list. United have a collection of nights they would rather forget, stretching from domestic shocks to European disasters.

Here are 10 of the most embarrassing defeats in Manchester United’s history.

EFL Cup second round, Blundell Park. Manchester United fielded a strong side against League Two opposition, yet they failed to find control and were dragged into a chaotic contest. 

Grimsby led 2-0 by half time, but United rallied back in the second half, forcing extra time and penalties. 

What followed was one of the longest shootouts in the club’s history, and one of their most humiliating exits. 

The Mariners held their nerve, winning 12-11 on spot-kicks, sparking wild celebrations among their fans and leaving United players and coaches stunned. 

Losing to a fourth-tier side was bad enough, but doing so in such dramatic fashion cemented the match as one of the darkest days in modern club history.

Liverpool handed United their joint-heaviest competitive defeat and biggest ever loss in this fixture.

Cody Gakpo, Darwin Núñez and Mohamed Salah all scored braces, with Roberto Firmino adding the seventh. United collapsed after half-time, conceding six in 45 minutes, and the result became the defining low of the post-Ferguson era.

The Louis van Gaal era was meant to restore order after the turbulence of David Moyes, but things started badly.

In August 2014, United travelled to League One MK Dons in the League Cup and were hammered 4–0. The performance was shambolic, with defensive errors and no cohesion.

It underlined how far the squad had declined in just a couple of years and remains one of United’s darkest nights in the competition.

Derby defeats always sting, but this one was devastating. City had started to emerge as genuine title contenders under Roberto Mancini, and their visit to Old Trafford in October 2011 was a chance to prove it.

They demolished United 6–1, with Mario Balotelli’s infamous “Why Always Me?” celebration lighting up the day, while United’s defence crumbled. The result signaled a power shift in Manchester that has only grown stronger over the years.

Losing to Liverpool is painful enough, but to be dismantled at Old Trafford by your fiercest rivals is another level of humiliation.

In March 2009, United were in fine form and favourites for the title, but Rafael Benitez’s Liverpool stunned them with a ruthless 4–1 win. Fernando Torres, Steven Gerrard and Andrea Dossena were all on the scoresheet, leaving United fans stunned and silenced in their own backyard.

While losing to Barcelona is not shocking in itself, the manner of this defeat was. In the Champions League quarter-final at Camp Nou, United were completely outclassed. Lionel Messi ran the show, David de Gea gifted a goal, and United looked nowhere near the elite level.

The 3–0 scoreline could have been worse, and it highlighted just how far the club had fallen on the European stage compared to the Ferguson years.

Early in the 2018–19 season, Jose Mourinho’s United were expected to make a statement against Tottenham at Old Trafford.

Instead, they collapsed to a 3–0 defeat in front of their home fans. What made it worse was Mourinho’s defiant post-match rant where he demanded “respect” for his three Premier League titles.

The result exposed the team’s weaknesses and intensified pressure on the Portuguese boss, who would be gone by December.

United’s Champions League campaign in 2011–12 should have been straightforward, but it ended in embarrassment.

Drawn into a group with Basel, Benfica and Otelul Galati, they were expected to qualify with ease. Instead, United slipped up in Switzerland, losing 2–1 to Basel in their final group game.

The defeat meant an early exit from Europe’s top competition, a shock for a club used to deep runs under Ferguson.

Few results in modern United history are as painful as this one. Under Ole Gunnar Solskjaer, United hosted Liverpool in October 2021 and were humiliated 5–0 at Old Trafford.

Mohamed Salah scored a hat-trick, Paul Pogba was sent off, and fans streamed out long before full-time. It was not just a heavy defeat but a brutal reminder of the gulf between United and Jurgen Klopp’s Liverpool at the time.

David Moyes’ disastrous spell at Old Trafford is well-known, but the problems did not end with him. On the opening day of the 2014–15 season, United, under new boss Van Gaal, suffered a 2–1 defeat to Swansea City at Old Trafford.

It set the tone for a turbulent campaign and left supporters frustrated that the team was struggling even against mid-table Premier League opposition.