Italy will miss their second World Cup in a row after slumping to a shock 1-0 play-off semi-final defeat to North Macedonia on Thursday.
Aleksandar Trajkovski's low drive in the second minute of stoppage time stunned the European champions in Palermo and set-up a qualifying final with Portugal in Porto on Tuesday for a chance to be in Qatar in November.
Roberto Mancini's side were loudly booed off after a defeat which means Italy will have to wait until at least 2026 to see its national team at a World Cup.
By then it will have been 12 years since the Azzurri's last participation in the world's biggest football tournament after they failed to qualify for the 2018 edition, also crashing out in the play-offs on that occasion.
Italy as predicted dominated the play but as has been the case in recent matches struggled to break down a resolute away side and when presented with chances were not clinical enough to take them.
The hosts should have been ahead on the half-hour mark when Domenico Berardi was gifted the ball on the edge of the area by goalkeeper Stole Dimitrievski.
The Sassuolo winger, who has been in red-hot form this season for his club, took too long to shoot and hit his effort into Dimitrievski's welcoming arms.
It was wave after wave of Italy attack but an initially vibrant crowd began to grow frustrated at their inability to carve out a clear opportunity to score, and it showed in a team which began to look desperate make the breakthrough.
Those fans were on their feet hailing an Italy hero seven minutes before the break, but it was for Alessandro Florenzi stopping Darko Churlinov from giving North Macedonia a shock lead after bursting through into a great scoring position.
Berardi looked Italy's biggest threat and went
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