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…