European champions Italy will not play in the 2022 World Cup after being stunned by North Macedonia in their play-off in Palermo.
Aleksandar Trajkovski picked up the loose ball in the 92nd minute, drove forward and fired a sensational winner from outside the area.
The goal sparked wild celebrations on the North Macedonia bench, while Italy's players and coaching staff dropped to their knees in front of their home fans.
It means Italy have failed to qualify for a second consecutive World Cup, ensuring the Azzurri will endure at least 12 years between appearances at football's showpiece event.
It is just eight months since Roberto Mancini's side celebrated one of their greatest triumphs - beating England at Wembley to win Euro 2020 having been considered outsiders going into the tournament.
But they have now paid the price for a disjointed - if previously unbeaten - World Cup qualification campaign during which they finished runners-up to Switzerland in their group, winning four and drawing four of their eight matches.
As expected Italy dominated possession on Thursday but failed to penetrate the resolute North Macedonia defence, registering five shots on target from 32 attempts.
The visitors, ranked 67th in the world, are rewarded for their defensive display with a play-off final against Portugal, who beat Turkey 3-1.
North Macedonia are 90 minutes away from reaching consecutive tournaments, having never reached a Euros or World Cup before qualifying for Euro 2020.
Four-time World Cup winners Italy, who are ranked sixth in the world, will watch events in Qatar in November and December from afar.
The shock of 2022
As the players emerged from the tunnel and the national anthems played, this was billed as a routine victory for Italy.
The mouth-watering prospect of veteran superstars Giorgio Chiellini and Portugal's Cristiano Ronaldo meeting in the play-off final loomed large.
But it was anything but routine.
Mancini's side started brightly and Marco Verratti kept them ticking, but they struggled to translate their possession into clear-cut chances.
North Macedonia came to Italy with a defensive gameplan and they threw everything in the way of the ball, as Visar Musliu caught the full force of a Domenico Berardi volley in the groin.
Berardi was a rare bright spark for Italy but when he was gifted possession by North Macedonia keeper Stole Dimitrievski, who had left his goal momentarily unguarded, the Sassuolo forward could not get the ball out of his feet in time to roll it into the net.
That theme continued into the second half as Berardi's movement again proved to be a threat without the final product.
As he rolled his marker just outside of the area with ease, he could only fire his effort over the bar with just the keeper to beat.
North Macedonia had just 34% possession and four shots over 90 minutes, but they took their opportunity against the run of play clinically.
As the ball bounced up inside the Italian half, Trajkovski, who used to play for Palermo, chested the ball away from two blue shirts and set off towards Gianluigi Donnarumma's goal.
The Paris St-Germain keeper had virtually nothing to do for 90 minutes, but he was too slow to react to Trajkovski's fizzing effort as it nestled into the bottom corner.
The journey is not yet complete for North Macedonia, who face Italy's predecessors as European champions in the final, but this is unquestionably the upset of the play-offs.
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