Manchester United have suffered one of their most humiliating losses in the club’s history after being knocked out of the League Cup by League Two side Grimsby Town.

Ruben Amorim’s team were playing in the second round of the competition for the first time in 11 years but just about took the Mariners to penalties after recovering from 2-0 down in the first half.

However, £65m summer signing Bryan Mbeumo missed from the spot and goalkeeper Andre Onana struggled in goal as Grimsby ran out 12-11 winners on penalties.

Following Sir Alex Ferguson’s Old Trafford departure in 2013, the defeat to Grimsby has to be the most embarrassing for Man Utd. But this isn’t a one off, with the Red Devils suffering some heavy and humiliating losses since 2013 under numerous managers.

Man Utd’s most embarrassing defeats since Sir Alex Ferguson left 11 Man City 4-1 Man Utd 2013/14

David Moyes was the man to replace Ferguson, and in October 2013, led his Man Utd side in the first Manchester derby at the Etihad.

However, the Red Devils, who were the defending champions, found themselves 4-0 down in 50 minutes and began the shift in power in Manchester.

10 MK Dons 4-0 Manchester United 2014/15

MK Dons hadn’t been founded the last time United played in the second round of the League Cup in 2014, but the League One side hammered Louis van Gaal’s side 4-0.

Two goals from Will Grigg put the third-tier side on their way, before Arsenal loanee Benik Afobe rounded things off late on with a brace of his own.

9 Everton 4-0 Manchester United 2018/19

Ole Gunnar Solskjaer and United were looking to finish in the top four when they travelled to Goodison Park to take on Everton in April in 2019.

However, the Red Devils failed to turn up, registering just one shot on target as they were outclassed by the Toffees, who went 4-0 up just after the hour mark. United would fail to qualify for the Champions League that season.

8 Manchester United 1-6 Tottenham 2020/21

Luckily for Man Utd and Solskjaer, the 6-1 defeat to Tottenham in October 2020 was played behind closed doors.

It was Jose Mourinho who came back to haunt the Red Devils, who conceded six at Old Trafford for just the second time in the Premier League. Spurs were 4-1 up at half time after Bruno Fernandes put United in front, and Tottenham coasted to victory as Mourinho got his revenge on United.

7 Manchester United 0-5 Liverpool 2021/22

A year on from a heavy defeat to Tottenham, Old Trafford was packed as Jurgen Klopp and Liverpool humiliated Solskjaer and Man Utd.

Mohamed Salah was the star of the show with a hat-trick for the visitors, with Naby Keita and Diogo Jota also getting on the scoresheet. Unfortunately for the Red Devils, though, things would only get worse against Liverpool.

6 Watford 4-1 Manchester United 2021/22

A heavy defeat at Vicarage Road against relegation-threatened Watford proved to be the final straw for Solskjaer as Man Utd manager in November 2021.

The Hornets, who would pick jump just 23 points all season and finish 19th, ran out comfortable winners, with captain Harry Maguire being shown a red card to cap things off for the Red Devils. Solskjaer left the club the following day.

5 Brighton 4-0 Manchester United 2021/22

Ralf Rangnick took interim charge of Man Utd following Solskjaer’s Old Trafford departure, but he had seen enough by the time his side were hammered by Brighton in May 2022.

Moises Caicedo, Marc Cucurella, Pascal Gross and Leandro Trossard were the goalscorers for the Seagulls on the day to end United’s slim chances of Champions League qualification.

4 Brentford 4-0 Manchester United 2022/23

With Erik ten Hag the new man in charge at Old Trafford, there was plenty of positivity in the summer of 2022.

However, that quickly evaporated as Brentford stunned the Red Devils by scoring four goals in the first half, even with Cristiano Ronaldo in the starting line-up.

It was also United’s seventh loss in a row away from home, their worst run since 1936, although that wasn’t Ten Hag’s fault.

3 Sevilla 3-0 Manchester United 2022/23

Heading into the second leg of the Europa League quarter-finals level at 2-2, United failed to show up in Spain as Sevilla ran riot with a 3-0 win after two goals from Youssef En-Nesyri and one from defender Loic Bade.

Errors at the back from Maguire and David de Gea, with nothing going forward, Ten Hag’s side exited Europe with a whimper.

2 Liverpool 7-0 Manchester United 2022/23

Man Utd’s worst ever result in the Premier League came at Anfield in March 2023, with Liverpool recording the biggest win in the history of the fixture between the two rivals.

Cody Gakpo broke the deadlock just before half time and Klopp’s side ran riot in the second half, scoring six times with braces from Gakpo, Darwin Nunez, Salah and one from Roberto Firmino.

It was the first time in over 90 years that Man Utd had conceded seven goals in a single match, with Ten Hag the manager in charge.