The unthinkable happened in Palermo on Thursday as the Azzurri were beaten 1-0 by North Macedonia following a last-gasp goal by Aleksandar Trajkovski in their playoff semifinal.
It was North Macedonia’s only real opportunity after a completely dominant performance by Italy, which missed a number of chances and had several others saved by visiting goalkeeper Stole Dimitrievski.
Italy also failed to qualify for the 2018 World Cup after losing to Sweden in a two-legged playoff. Missing two straight World Cups is an unprecedented low point for the four-time champion, especially just months after winning Euro 2020.
North Macedonia will play Portugal on Tuesday for a spot in the tournament in Qatar after Cristiano Ronaldo’s side beat Turkey 3-1. Euro 2020 is the only major tournament North Macedonia has qualified for.