The shock Carabao Cup elimination at Blundell Park was the latest of many painful defeats the Red Devils have had to endure in the last 25 years
They say that when you hit rock bottom, the only way is up. But Manchester United fans have learned that that is simply not true; even when you think that things couldn't possibly get any worse, they can and often do.
Ruben Amorim had promised Red Devils' fans after their worst season in 52 years that the good time were coming, but three matches into the new campaign and the club appear to be sinking even further into the abyss, especially after Wednesday's shock elimination from the Carabao Cup at the hands of Grimsby Town of League Two.
It marked only the second time that United had been knocked out of the League Cup in the second round in 30 years, and it was arguably the worst defeat of Amorim's dismal nine-month spell in charge. And yet it was just one of many abysmal results inflicted on the club in the last 25 years.
GOAL ranks the worst defeats United have endured in all competitions in the 21st century…
Getty Images15Manchester United 1-2 Manchester City | February 10, 2008
Despite the presence of Cristiano Ronaldo, Carlos Tevez, Nani and Ryan Giggs, Sir Alex Ferguson's Red Devils were unable to overpower Manchester City. Sven-Goran Eriksson's team beat United on home soil in the second week of the campaign, but the defeat at Old Trafford the following February was particularly painful.
The match came just days after the 50th anniversary of the Munich air disaster, but Ferguson's team fell behind through goals from Darius Vassell and Benjani. Michael Carrick scored late on for United, but they were unable to rescue a point.
AdvertisementGetty Images14Brighton 4-0 Manchester United | May 7, 2022
The wheels had well and truly fallen off under Ralf Rangnick by the time United made the trip to Brighton near the end of the 2021-22 season. Moises Caicedo, Marc Cucurella, Pascal Gross and Leandro Trossard all scored in the first hour at the Amex Stadium as the Red Devils were crushed by Graham Potter's team.
They went on to draw with Chelsea and lose to Crystal Palace in the final two games of the season as they scraped to a sixth-placed finish in the top-flight.
Getty Images13Manchester United 0-3 Manchester City | March 25, 2014
If losing 4-1 away to City in the third week of the Premier League season wasn't bad enough, David Moyes' spell in charge got even worse when the Red Devils were hammered by their noisy neighbours on home soil. Edin Dzeko opened the scoring in the first minute before adding a second just before the hour mark while Yaya Toure then completed the destruction towards the end.
City went on to win the title while United finished in seventh place, and Moyes went on to say that his team must aspire to be at their cross-city rivals' level, an assertion that did not go down well with United's fans.
Getty Images12Manchester United 1-4 Liverpool | March 14, 2009
It was all going so well when Cristiano Ronaldo put United ahead after 22 minutes at Old Trafford. The fun did not last long, though, as Fernando Torres equalised before the half-hour mark. Steven Gerrard, Fabio Aurelio and Andrea Dossena then completed the turnaround and the humiliation, as Liverpool claimed a 4-1 win at Old Trafford.
The Reds beat United twice in the league that season as they kept them under pressure in the title race, but in the end the Red Devils finished four points clear and lifted the Premier League trophy yet again.
