Giorgio Chiellini's first-half goal was cancelled out by Aleksandar Trajkovski as Italy struggled to a 1-1 draw against Macedonia in Turin on Friday, condemning the four-time champions to the World Cup play-offs.
Italy now sit second in their qualifying group, three points behind Spain with just two matches remaining.
Italy have 20 points in Group G and their hopes of reaching Russian Federation now rest on finishing as one of the best eight runners-up who progress to the playoff round from the nine European groups.
A mutual lapse in discipline marred the second half, with three players booked needlessly, and Italy were unable to build momentum in their pursuit of another goal. I had moments that were positive and negative, like all coaches. We're already playing for the playoffs.More news: Google Is Using Balloons to Restore Phone Service in Puerto Rico
Confidence was low after last month's 3-0 loss in Spain but, despite winning only 3-2 in Skopje previous year thanks to a stoppage-time goal, Italy was expected to easily sweep away Macedonia in Turin. "I think the whistles were deserved, even if I think you should never jeer the national side as a point of principle".
"We need to get the crowd on our side because they can help us".
Italy failed to click after halftime and were given a first warning when Gianluigi Buffon had to smother a header from Ilija Nestorovski.
It was more of the same in the second half with Macedonia content to sit back and wait for an opening.More news: Redistricting lawsuit may be too late for 2018
He told reporters: "If we play like we did in the second half then we will struggle to get through the play-offs".
"We're really frustrated. We are sorry for the fans, we understand them and we are as upset as they are, but I am sure they will support us when we need them", said Chiellini.
"That made a big difference and when that drops, the sharpness goes", he said.
Failing to reach the World Cup for the first time since 1958 would certainly bring a swift end to his tenure.More news: Slight Chance Of Rain Today; Storms By Saturday
Spain cruised to a 3-0 win over Albania on Friday to secure qualification for the World Cup and put Italy on a path for the playoffs.