Four time World Cup winners Italy lost 1-0 to Sweden in Solna in the first leg of their World Cup play-offs.
Jakob Johansson scored the match winner in the 61st minute of the encounter, firing home from 20 yards via a Daniele de Rossi deflection after the first half ended goalless.
The game was the Italy’s first World Cup play-off since 1997, which was also Gigi Buffon’s senior debut, and they have not missed this tournament since 1958.
Marco Verratti was booked for a lunging tackle on 28 minutes and will be suspended for the second leg at San Siro on Monday.
Italy were slightly improved after the break but they were still disappointing in converting their chances.
Manchester United’s Matteo Darmian came closest to equalising in the 74th minute but his shot hit the post.
Italy will need to turn the tie around in Monday’s second leg at the San Siro to reach the World Cup in Russia.
Inter Milan winger Antonio Candreva also caused danger twice straight after the restart, his ball flashing across the face of goal and then a strike palmed out from the near top corner by Robin Olsen.
Lorenzo Insigne replaced Verratti for the final 15 minutes, but never threatened.