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 defense, 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.