• Italy also failed to qualify for the 2018 World Cup after losing to Sweden in a two-legged playoff the previous November.
• Overall, Italy had 32 shots on goal, compared to just four for its opponent.
In a major upset, European champions Italy have failed in their bid to reach the World Cup... again.
They were beaten 1-0 by North Macedonia in a play-off semi-final to qualify for the tournament, which takes place in Qatar from 21 November.
Aleksandar Trajkovski scored a last-gasp goal for North Macedonia.
It was North Macedonia’s only real opportunity after a completely dominant performance by Italy, which missed a number of chances and had several others saved by visiting goalkeeper Stole Dimitrievski.
Overall, Italy had 32 shots on goal, compared to just four for its opponent.
But, just like five years ago, at the final whistle the Italian players fell to the ground in disbelief and disappointment — with several of them in tears — as the opposition celebrated wildly.
Italy also failed to qualify for the 2018 World Cup after losing to Sweden in a two-legged playoff the previous November. Missing two straight World Cups is an unprecedented low point for the four-time champion, especially just months after winning Euro 2020.
“I'm proud of my teammates, we are all destroyed and broken but we have to start again,” Italy captain Giorgio Chiellini 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.”
But Roberto Mancini, who took over as Italy coach after the last qualifying failure, said on Thursday that the disappointment “was too great to talk about the future”.
“I feel that just as last July was the best thing I experienced at a professional level, this is the greatest disappointment,” Mancini added.
North Macedonia will play Portugal on Tuesday for a spot in the tournament in Qatar after Cristiano Ronaldo’s side beat Turkey 3-1.
Euro 2020 is the only major tournament North Macedonia has qualified for.
Mancini was missing a number of players that helped Italy win the European Championship last summer and had to field a makeshift defence, but it was barely troubled by North Macedonia until the very end.
Italy got off to an aggressive start but struggled to find a way past the wall of red shirts.
The Azzurri were gifted a great chance in the 30th minute after a horrendous kick from the North Macedonia goalkeeper left Domenico Berardi with an open goal but he scuffed his shot and Dimitrievski got back in time to make the save.
Dimitrievski did better moments later when he fingertipped Ciro Immobile’s angled shot over the bar.
Italy was getting closer and Dimitrievski had to make another save, this time to palm Lorenzo Insigne’s effort around the post.
North Macedonia had its first attempt on goal on the stroke of halftime when Enis Bardi threaded a ball through for Trajkovski but his effort was straight at Gianluigi Donnarumma.
Berardi almost atoned for his first-half error early in the second period but saw one attempt well saved by Dimitrievski and curled another just past the left post.
Italy was laying siege to the goal but saw everything charged down by North Macedonia.
And it was made to pay for its profligacy in stoppage time as Trajkovski fired a low shot into the bottom left corner from 25 yards, leaving Mancini looking stunned on the sideline.