History was made at the Stadio Renzo Barbera in Palermo on Thursday night as North Macedonia, ranked 131st in the world by FIFA, eliminated Euro 2020 champions Italy from World Cup qualification.
Italy dominated the tie with an incredible 32 attempts, but very few of those chances were a threat to North Macedonia, who limited the Italians to long-distance efforts.
Rayo Vallecano goalkeeper Stole Dimitrievski was in fine form to keep Italy out and the home side grew increasingly frustrated as the clock counted down.
North Macedonia posed little to no threat to Italy, with their first shot coming on 45 minutes and failing to register a single attempt inside the Italian penalty box.
The decisive moment, though, came two minutes into stoppae time as a long ball forwards from a goal kick caused chaos in the Italy defence. That allowed for substitute Bojan Miovski to head the ball on and it fell to Aleksandar Trajkovski, who beat Gianluigi Donnarumma from 25 yards.
His finish into the bottom corner of the net stunned the fans in attendance in Palermo and that goal will likely have ramifications for Italy and their coach Roberto Mancini.
Having won Euro 2020 only nine months ago, Italy are ranked sixth in the world in FIFA rankings yet will not be among the 32 teams present in Qatar in November.
North Macedonia will now face Portugal after they overcame Turkey with a 3-1 win in another qualification playoff semi-final.,