Italy failed to secure a World Cup play-off spot as they were held to an uninspiring 1-1 draw with Macedonia at the Stadio Olimpico.
Victory would have assured Gian Piero Ventura's side of another chance to qualify behind group winners Spain, but they were unable to see out a win in Torino.
The Azzurri barely got out of second gear against their stubborn visitors but took a first-half lead through Giorgio Chiellini.
They were made to pay for their sluggish second-half display when Palermo forward Aleksandar Trajkovski lashed home in the 77th minute to claim a memorable point for Igor Angelovski's side.
Italy travel to Albania on Monday for their final Group G game and will want a significantly improved performance to try to secure a play-off spot.
The Azzurri, captained by Gianluigi Buffon wearing their traditional blue shirt on his 172nd international appearance, looked sharp in the early stages and should have been ahead inside eight minutes.
| A strange sight, but a beautiful one! October 6, 2017
Ciro Immobile and Lorenzo Insigne combined cleverly on the edge of the Macedonia area to allow the latter to break through a static defence and force Stole Dimitrievski into a smart save.
Macedonia, clearly not content to sit back and soak up pressure, carved out an excellent opportunity of their own 10 minutes later, but Goran Pandev's crisp volley was well held by Buffon.
Italy then wasted two glorious opportunities to take the lead.
Insigne met Marco Parolo's clipped cross in the middle of the area but his header lacked direction and was gathered by Dimitrievski.
The Macedonia goalkeeper should have been called into action again shortly after when Davide Zappacosta pulled down a deep cross inside the area. The Chelsea defender scuffed his half-volley horribly over, though.
The mounting pressure paid off five minutes before the break as Chiellini scored his eighth goal for his country.
Insigne sliced open the Macedonia defence with an incisive pass into the path of Immobile, who slid in a first-time cross for the Juventus defender to coolly slot through the legs of Dimitrievski.
The second half was played out at a pedestrian pace with the first attempt on goal not coming until the 64th minute. Stefan Spirovski tried his luck from distance, but Buffon was equal to his sweetly struck shot.
The Juventus stopper was in the right place again a few minutes later to keep out Ilija Nestorovski's header from a teasing cross.
Macedonia's positive second-half display was rewarded 13 minutes from time when Trajkovski latched onto Pandev's throughball to fire an unstoppable shot past Buffon into the bottom-left corner.
Substitute Federico Bernardeschi drilled a long-range effort wide in the closing stages, but three points would only have served to flatter Ventura's side after a hugely disappointing performance.
