Italy missed out on a second consecutive World Cup after losing 1-0 at home to North Macedonia, with Aleksandar Trajkovski scoring the winner in second-half stoppage time.
European champions Italy did not qualify for the World Cup four years ago, their first failure to reach the tournament since 1958, but they dominated from the off in Palermo and looked on course for victory.
The hosts became more desperate in their search for a winner after the break as chances continued to come and go before, in stoppage time, Trajkovski arrowed in a stunning winner to spark wild North Macedonian celebrations.
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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 play-off final on Tuesday – live on Sky Sports – for a place at the World Cup.
“It is a huge disappointment,” Italy midfielder Jorginho told Rai Sport. “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 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.