Italy confirmed their place in the World Cup play-offs but were booed off the pitch after their 1-1 draw with Macedonia.
Giorgio Chiellini’s opener in Turin was cancelled out by substitute Aleksandar Trajkovski’s second-half finish as Gian Piero Ventura had to settle for second place in Group G.
Spain’s 3-0 win at home to Albania and Italy’s failure to do so means the Iberians have booked their place in Russia next summer, but the Azzurri now face a two-legged play-off to reach the tournament.
Ventura’s side needed just a point from its final two qualifiers against Macedonia and Albania but confidence was low after last month’s 3-0 loss in Spain.
Despite luckily winning 3-2 in Skopje last year thanks to a stoppage-time goal and a missed Macedonian penalty, Italy was expected to easily beat Macedonia in Turin, at least on paper.
However, they struggled to carve out opportunities.
The hosts sported their away strip to allow veteran goalkeeper Gianluigi Buffon the chance to wear the famous blue home shirt on his 172nd appearance, a European record.
He watched his team-mates make a bright start and they could have been in front after just seven minutes.
Lorenzo Insigne was well-placed to fire a right-footed shot from Ciro Immobile’s through-ball but Stole Dimitrievski was equal to the effort.
During an open first 20 minutes, Goran Pandev met Marjan Radeski’s cross to nearly put Macedonia ahead but Buffon sprung to his right to tip his header around the post.
Macedonia were the better side in the second period, with Stefan Spirovski setting his sights from range after 64 minutes and testing the hands of Buffon once more.
Two minutes later, Ilija Nestorovski fired wide from a tight angle, before Pandev blazed high and wide as it looked as though Macedonia would rue their missed opportunities.
But Pandev, who still plies his trade in Italy with Genoa after a long career in Serie A, turned provider for Trajkovski to fire a deserved equaliser into the bottom left corner with 13 minutes remaining.
Both sides had chances to seal all three points as Davide Zappacosta and Federico Bernardeschi both shot wide for the Azzurri, while Ivan Trickovski’s header from Enis Bardhi’s cross went agonisingly close.