Italy have failed to qualify for the 2022 World Cup following a shock 1-0 defeat by North Macedonia on Thursday.
For the first time in their history, the Azzurri will miss out on successive finals after Aleksandar Trajkovski struck a stoppage-time winner at Renzo Barbera.
Roberto Mancini’s side triumphed at Euro 2020 just eight months ago, defeating England on penalties in the final to claim their second title.
But four years after their playoff defeat by Sweden denied them a place in Russia, they will be absent in Qatar after suffering their first ever loss on home soil in a World Cup qualifier.
It is fair to say it has been quite the journey from one World Cup qualifying failure to another.
Swede success
Despite finishing behind Spain in their qualifying group, Italy were heavy favourites to overcome Sweden in a two-legged playoff.
However, Jakob Johansson struck the only goal of the opening leg to set up a tense climax in Milan.
The Azzurri dominated their opponents, but the Swedes stood firm to deny them a place at the World Cup finals for the first time since 1958.
Euro 2020 glory
Failure to qualify for Russia culminated in the departure of Gian Piero Ventura, who was replaced in the hot-seat by Mancini.
Despite winning just one of his first six matches in charge, things eventually clicked into gear for the former Inter and Manchester City coach, who oversaw a perfect qualifying campaign for the delayed Euro 2020.
The Azzurri came flying out of the blocks; topping Group A with maximum points before seeing off Austria, Belgium and Spain, before holding their nerve to overcome England on penalties for a second European crown.
The record-breaking run
In fact, Italy did not look back after a 1-0 defeat by Portugal in the Nations League in September 2018.
The Azzurri subsequently embarked on a record-breaking 37-match unbeaten run across all competitions spanning three years.
The streak came to an end following a 2-1 defeat by Spain in the Nations League semi-finals last October.
North Macedonia mayhem
Despite going unbeaten in qualifying, four draws from their last five matches meant Italy had to settle for second place in Group C and another playoff berth.
Once again, the Azzurri were red-hot favourites to overcome North Macedonia, who are seeking their first appearance at the finals as an independent nation.
But despite 32 attempts on goal, the hosts were unable to make their superiority count in Palermo, and were punished right at the death as the visitors stunned the four-time world champions.