The Azzurri suffered a shocking 1-0 defeat at home to North Macedonia, courtesy of a stoppage-time stunner from Aleksandar Trajkovski on Thursday night.
It means the reigning European champions have not qualified for football's biggest event since 2014 and will be forced to wait at least 12 years between World Cup appearances.
While awful for Italy, their failure might have brought a smile to English faces.
Not just because Italy were triumphant over the Three Lions in the Euro 2020 final, but because of the celebrations which followed.
Veteran defender Leonardo Bonucci filmed himself signing 'It's coming Rome', in what many considered a swipe at England's famous 'Three Lions' anthem.
For a brief moment, at least, it's England's turn to be smug, having sealed automatic qualification for this winter's tournament in Qatar.
Reacting to Italy's exit, ex-Crystal Palace chairman Jordan said: "A lot of my friends are Italian, so I find it very hard to have anything but delight in the demise of the Italian team!
"I've had to listen to all their claptrap for the last 12 months.
"So I find it very hard to have any empathy with the Italians, they're such a magnanimous bunch!"