Italy will miss successive World Cups for the first time since 1958.
Italy hosted North Macedonia in Palermo for a chance to progress to the next round of the playoffs and seal a spot at the FIFA 2022 World Cup in Qatar, but fell in the closing stages of the game to the European minnows.
North Macedonia has been on the up in European football in recent years, starting with their qualification for the UEFA Euro 2020 tournament, where they also showed glimpses of their quality but were outshone by the more experienced European teams.
However, no one expected this upset but they delivered it to the Italians in front of their own fans, causing the stadium to fall into a loud silence.
Italy manager Roberto Mancini was bereft of words after the shocking defeat which will leave the Azzurri out of the World Cup for a second straight tournament.
Aleksandar Trajkovski's 92nd minute goal after a strong defensive performance from North Macedonia did the damage, inflicting Italy's first defeat in 60 home matches in the World Cup qualifiers.
North Macedonia will now take on Portugal on Tuesday, who brushed Turkey aside 3-1 in their own fixture, for one of the three remaining UEFA spots in the 2022 World Cup.
Manager Mancini had no words to describe the feeling of a second successive World Cup miss. "It's hard to say something right now, I don't know what to say," Mancini told reporters.
"Last summer was the most beautiful joy [referring to Italy's Euro 2020 win], now comes the greatest disappointment. It is not easy to think of other things, I am very sorry for the boys: I love them much more tonight than in July.
"I am the coach, I am the first responsible, the boys are not. They have a great future, they are strong players for the future of the national team. We did not deserve this defeat."
Italy's wastefulness causes them a golden opportunity
The Azzurri had 32 shots at goal while North Macedonia had a measly five. However, it was the defensive solidity and wastefulness of the Italians, more than any form of heroics from the North Macedonian goalkeeper Stole Dimitrievski, that cost Italy the game.
Blocked shots and wild off target attempts led to Italy not being able to score a goal, leaving it all to North Macedonia to score with their clearest shot on goal, from Trajkovski's boot.
Azzurri team captain, Giorgio Chiellini, who was hoping to make it to another World Cup before retiring from international duty will not get the chance again.
Nevertheless, he said after the match that he was proud of his Azzurri teammates. "I'm proud of my teammates, we are all destroyed and broken but we have to start again,'' he said. "At the moment it's difficult to talk about it, it will remain a great hole.
"I hope that the coach will stay because he is essential for this team. Now we have to return to winning, go to the Euros and in four years time return to this blessed World Cup.''
On the other hand, North Macedonia's coach Blagoja Milevski was beside himself with joy, pointing out the irony of his team's victory over the Italians.
"We won Italian style against the Italians, a goal with two shots on target," he told reporters. "I'm very happy for this victory, I'm proud for these guys."
Jorginho: Penalty miss will haunt me for the rest of my life
Italy had to contend in the playoffs in the first place because Jorginho missed two penalty kicks in their last game of the regular qualifiers against Switzerland.
More wastefulness led to their downfall against North Macedonia, and the Chelsea midfielder has admitted that things could have been different if he had scored that penalty.
“It is difficult to explain what happened,” Jorginho told RAI Sport through tears.
“It hurts so much. I’ll be honest, I am still incredulous. I don’t think we lacked creativity, as we always dominated matches and created so many chances. Unfortunately, we were unable to finish them off.
“We played good football, we won the European Championship last summer, but unfortunately in the last few games we made small errors and were unable to recover from them. They made the difference.”
“It hurts when I think about it, because I do still think about it and it will haunt me for the rest of my life. Stepping up there twice and not being able to help your team and your country is something that I will carry with me forever, and it weighs on me.
“People say we need to lift our heads and carry on, but it’s tough.”
Meanwhile, Marco Veratti, said that the team have to question themselves after the strange capitulation. “Looking around the locker room, we had the players to challenge for the tournament itself, yet here we are talking about a disaster. It’s so tough to go from hero to zero.
“We experienced special times together and I will always be proud of my teammates. This is football, you need to score goals. We didn’t manage it, but we gave everything we had. It wasn’t enough.
“We have to ask ourselves questions now. There’s some bad luck, but you also need to make your own luck.”