November 13, 2017 went down as one of the worst days in the history of Italian football.

Urged on by over 70,000 home fans at the San Siro Stadium in Milan, four-time World Cup winners Italy were inexplicably stunned by Sweden in their do-or-die play-off and failed to qualify for football's biggest showpiece event for the first time since 1958.

Despite dominating in possession and creating a plethora of scoring opportunities in the clash, Italy lacked the cutting edge they needed to find a winner, while Sweden stood tall amid incessant onslaught and booked an incredible ticket to Russia with a 1-0 win on aggregate.

No one could have predicted the inconceivable would happen again.

However, the reigning European champions missed their second World Cup in a row on Thursday night after being beaten by North Macedonia 1-0 in the play-off semi-final in Palermo.

Just five years ago, Italy dominated from the off and had 32 shots on goal in front of their home fans, but on Thursday the visitors held their nerves and earned a famous victory after Aleksandar Trajkovski, who spent a total of four seasons in Palermo earlier in his career, broke Italian hearts with a sensational long-range goal.

It's just eight months since Italy outclassed England at Wembley to win the Euro 2020 having been considered outsiders going into the tournament. But they have now crashed back down to earth and paid the price for another harrowing performance.

"It's hard to explain, it's such a huge disappointment," captain Giorgio Chiellini told reporters post-game. "We've made mistakes since September and we've paid for them. We're distraught. At the moment it's difficult to talk about it, it will remain a great hole."

The sentiment was echoed by football legend Gary Lineker, who holds England's record for goals in the World Cup. "For Italy to go from being European Champions to not even making the final playoff stage is an almighty and devastating fall," the veteran tweeted.

The result was also a huge blow to coach Roberto Mancini, who just signed a new-four year contract extension with Italy following their triumph at Euro 2020. The 57-year-old is no longer certain about his position at the helm.

"Now I feel too disappointed to speak about my future, we will see," Mancini told a press briefing. "If last July was the best thing I had professionally, I think this is the biggest disappointment. You can't say anything. This is football. Sometimes incredible things happen and tonight it's happened."

"This is a group with great players and I'm sorry because we didn't deserve it. I think that the victory of the European Championship was deserved, then luck turned into total bad luck," he added. "On a human level, I can say that I love the boys more tonight than in July. It is a time of great difficulty and therefore my affection is even greater."

For North Macedonia, the journey is not yet complete. Next up for them is the Euro 2016 winners Portugal, who defeated Turkey 3-1 at home.

Cristiano Ronaldo's dream of World Cup glory remains alive after his teammates Otavio, Diogo Jota and Matheus Nunes put Portugal in control. Turkish talisman Burak Yilmaz missed a penalty five minutes from full-time that would have drawn the sides level.

Elsewhere, Sweden secured a 1-0 win over the Czech Republic and set up a clash away to Poland next Tuesday, while Real Madrid star Gareth Bale scored two brilliant goals to take Wales a step closer to qualifying for their first World Cup since 1958. Wales will now face Scotland or Ukraine in their play-off final.

In Asia, Japan qualified for a seventh straight World Cup by swatting aside Australia 2-0. Substitute Kaoru Mitoma netted two late goals for Japan after Takumi Minamino came close on several occasions.

Saudi Arabia also booked a ticket to Qatar despite being held by China, who remain one place from bottom in their group. Saleh Al Shehri put the Saudis ahead at the end of the first half, but Zhu Chenjie's penalty salvaged a draw.