Aleksandar Trajkovski's low force within the second minute of stoppage time stunned the European champions in Palermo and set-up a qualifying very last with Portugal in Porto on Tuesday for a danger to be in Qatar in November.
Roberto Mancini's facet were loudly booed off after a defeat which means Italy will must wait until at least 2026 to look its country wide crew at a World Cup.
By then it's going to had been 12 years because the Azzurri's closing participation inside the global's largest soccer match after they didn't qualify for the 2018 version, also crashing out within the play-offs on that event.
Italy as anticipated dominated the play but as has been the case in latest fits struggled to break down a resolute away aspect and whilst provided with chances had been now not clinical enough to take them.
The hosts must had been in advance at the 1/2-hour mark while Domenico Berardi changed into gifted the ball on the threshold of the location by goalkeeper Stole Dimitrievski.
The Sassuolo winger, who has been in crimson-hot form this season for his club, took too long to shoot and hit his attempt into Dimitrievski's welcoming palms.
It became wave after wave of Italy assault but an initially vibrant crowd started to develop annoyed at their inability to carve out a clean possibility to attain, and it showed in a group which started out to look desperate make the leap forward.
Those fans were on their ft hailing an Italy hero seven mins before the smash, however it changed into for Alessandro Florenzi stopping Darko Churlinov from giving North Macedonia a surprise lead after bursting via right into a extremely good scoring function.
Berardi regarded Italy's biggest hazard and went close 3 instances within the space of 5 five second-half mins, first hitting a weak shot at Dimitrievski earlier than curling every other one just extensive seconds later.
