The Euro crown appears a distant memory for Italy after they were denied a berth in the World Cup finals for a second successive time on Thursday.

If it was Sweden who had eliminated Italy for the 2018 World Cup in Russia, this time it was North Macedonia, ranked 67th in the world, who played dogged football like Italy have for so many years. The North Macedonians defended with their backs to the wall for 90 minutes before producing a stoppage time coup to edge out the Azzurri 1-0 in a playoff in Palermo for the finals in Qatar later in the year.

The rank outsiders now head to Tuesday’s final at the Estádio do Dragão in Porto with the hope that, having knocked out the European champions of 2020, they can do the same to Portugal, triumphant at Euro 2016. North Macedonia, formed after the break-up of Yugoslavia in 1991, has never made it to the World Cup finals.

The game was deadlocked 0-0 till 90 minutes when North Macedonia’s Aleksandar Trajkovski, who plays in the Saudi league with Al-Fayha, came up with his ambush of a goal in the second minute of added time, driven in after no Italian had met or cleared a ball heaved upfield by their goalkeeper, Stole Dimitrievski.

Italy, fifth in the Fifa world rankings, had 32 shots on goal, compared to just four for its opponent, commanded 70 per cent possession and had 16 corner kicks to nil for the visitors. Trajkovski’s route-one goal was North Macedonia’s only real opportunity after a completely dominant performance by Italy, who missed a number of chances and had several others saved by Dimitrievski.

North Macedonia coach Blagoja Milevski acknowledged the irony of their last-gasp victory.

“We won Italian style against the Italians, a goal with two shots on target,” he told reporters. “I’m very happy for this victory, I’m proud for these guys.”

For a country who have won the World Cup four times, Italy’s recent record is a national embarrassment, more so just eight months after lifting the Euro trophy at London’s Wembley.

Since winning their fourth World Cup trophy in 2006, they have not played a knockout game in the showpiece event, having only won one group stage match in the finals, against England in 2014, in that time.

In their qualifying group for Qatar, they came second to Switzerland, having drawn four of their last five games. Among them was a 1-1 stalemate with the Swiss, during which Italy’s Chelsea midfielder Jorginho missed two penalties that would have seen the Azzurri displace their opponents in top spot. And for the first time in their history, they will be missing from the finals of two World Cups in succession.