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Follow UsItaly missed out on the World Cup finals again after losing 1-0 at home to North Macedonia in their playoff semi-final as Aleksandar Trajkovski's last-gasp strike earned the visitors a famous win.
Italy did not qualify for the World Cup four years ago, missing out for the first time since 1958, but the European champions dominated from the off in Palermo. The hosts became more desperate in their search for a winner after the break, however, as chances continued to come and go before, in stoppage time, Trajkovski arrowed in a stunning winner to spark wild North Macedonian celebrations.
Roberto Mancini's Italy side had 32 efforts at goal in the match but somehow fell short, with North Macedonia going on to play Portugal in the playoff final on Tuesday for a place in Qatar.
"It is a huge disappointment," the Italy midfielder Jorginho said. "It hurts, it hurts so much. We have always created and dominated matches but we have not been able to finish teams off. It is not to blame anyone in particular but it is the reality.
"I don't know why we haven't been able to do this, I am also involved in this, and it hurts me to think about it."
Without the veteran pairing Leonardo Bonucci and Giorgio Chiellini through injury, Italy's makeshift defence was barely troubled in the first half, as all the action took place down the other end.
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Domenico Berardi had the best of the openings, having been presented with the ball after the North Macedonia goalkeeper Stole Dimitrievski misplaced a pass, but his shot was tame, with Dimitrievski getting back to make the save. Ciro Immobile also wasted a glorious first-half chance for Italy when blazing over the bar from a good position.
With their only meaningful attack of the match North Macedonia seized their chance. Italy did not look to be in too much danger, but Trajkovski, who plays in Saudi Arabia for Al-Fayha, wrote his name into North Macedonian football folklore with a shot that crept inside the post to stun the home fans.