MARCH 25: 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.
With inputs from BBC
ROME June 20 :Italy made it three wins from their Euro 2020 three Group A matches without conceding a goal as they beat Wales 1-0 on Sunday evening in Rome.
The Italians controlled the match from start to finish, giving the Welsh few options in either midfield or attack and after now withnot conceding a goal in over 1,000 minutes football, they have to be considered serious candidates for this year's European Championships.
With his side already assured of their place in the last 16, Italy coach Roberto Mancini made eight changes to the team that beat Switzerland in their first game and although his side maybe lacked some of the fluency of their wins against Turkey and the Swiss, Italy still controlled the game.
Marco Verratti was running the midfield, where the Welsh were keeping things tight, but struggling to string any moves together and all of the chances fell to Italy with Andrea Belotti firing just wide, before Verratti also sent effort the wrong side of Danny Ward's post.
Federico Chiesa flashed an effort across the face of goal and although Ward hadn't been forced into a difficult save, a goal looked to be coming. It arrived in the 39th minute when Matteo Pessina got a neat flick on Verratti's low free kick to send the ball in at the far post.
Another free kick early in the second half saw Italy again cause danger with Federico Bernardeschi rattling the woodwork, before Joe Allen almost found himself through on goal at the other end, before getting his feet in a tangle as he was caught in two minds what to do.
The Welsh were down to 10 men in the 55th minute when Ethan Ampadu was shown a straight red card for a late challenge that saw him plant his studs on the top of Bernardeschi's foot.
Chiesa found space on the right in the 59th minute, but Ward did well to keep Belotti's effort out as Italy kept up the pace looking for a second goal.
Another corner from Verratti caused problems for the Wales defense, before Bale smacked a volley over the bar in his side's best (and basically only) chance of the game. The Wales' captain was subbed shortly afterwards, perhaps to reserve him for the knockout phase as his side also progress to the next phase.
Meanwhile Mancini showed his confidence by replacing goalkeeper, Gianluigi Donnarumma in the 88th minute with Salvatore Sirigu on for the closing moments of the game.
(Xinhua)
ROME, June 16 Italy became the first side to assure their place in the knockout stages of Euro 2020 thanks to a 3-0 win against Switzerland in Rome on Wednesday.
The result means they will now contest top spot in Group A in their final group game against Wales, who beat Turkey earlier in the day.
Manuel Locatelli was Italy's hero with two goals as Roberto Mancini's side produced another assured and aggressive display of attacking football.
In Group A's other match at the Olympic Stadium in Baku, Aaron Ramsey and Connor Roberts each scored a goal for Wales as they won 2-0 against Turkey.
Both sides traded attacks in the first half, but Wales looked more dangerous in front of goal and marked the opener on 42 minutes when Ramsey chested down Gareth Bale's chip into the box before tapping the ball past Turkey goalkeeper Ugurcan Cakir.
Turkey's Burak Yilmaz should have restored parity early in the second half, but the captain wasted a golden chance from close range following a corner. At the hour mark, Wales were awarded a penalty but Bale put the spot-kick over the bar.
Bale had a large share in Wales' second goal though, as the striker danced through Turkey's penalty box before squaring to Connor Roberts, who sealed the deal in the dying seconds of injury time.
Elsewhere on Wednesday, Russia wrapped up their first victory in Group B after beating Finland 1-0 thanks to a goal from Aleksey Miranchuk on home soil in Saint Petersburg.
Finland started their second game in a lively manner, as Joel Pohjanpalo looked to have broken the deadlock with only five minutes played but the striker's opener was flagged offside.
Russia needed some time to gain a foothold into the contest but took a deserved lead through Miranchuk, who benefitted from Artyom Dzyuba's good build-up work before curling the ball past Finland goalkeeper Lukas Hradecky and into the top-left corner.
After the break, Russia continued on the front foot while Finland were lacking in attacking ideas.
Russia remained the more dangerous outfit and they should have added more goals to their lead, but Rifat Zhemaletdinov and Daler Kuzyaev failed to score from promising positions.
(Xinhua)
ROME, June 11 : Italy started their Euro 2020 campaign with an easy 3-0 win against Turkish side in the Olympic Stadium in Rome on Friday evening.
Italy looked sharp from the beginning with Roberto Mancini's favored 4-3-3 formation.
Giorgio Chiellini's powerful header from a corner was tipped over by Turkish keeper, Ugurcan Cakir, who was impressive all game. Moments before the halftime whistle, Italy had a good penalty appeal rejected after Leonardo Spinazzola's cross clearly hit Zeki Celik's arm.
Turkey produced very little in attack in the first half and things didn't change much after the break, although Cengiz could have done better than see his shot blocked after a rare break.
Italy took a deserved lead in the 53rd minute when they finally found a 3 against 3 in attack and Domenico Berardi found space on the right with options to cross or shoot. He opted to drill the ball across the area and the ball rebounded off Merih Demiral into his own net. It was bad luck for the defender, who plays for Juventus.
The goal left Turkey groggy and Italy began to pepper their goal with shots, first Spinazzola was denied by Cakir, before Lorenzo Insigne saw a shot deflected over.
Ciro Immobile doubled Italy's lead in the 66th minute as he slotted home from close range after Cakir had blocked Spinazzola's shot.
Insigne netted a third in the 79th minute with a curling shot after a wonderful pass.
With inputs from Xinhua
ROME, June 12: Italy waited a long time for this European Championship to start and then showed Friday just how eager the team was to play the tournament opener.
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