Four-time World Cup winner Italy was stunned in Palermo as Aleksandar Trajkovski — who used to play club soccer in the Sicilian city — fired past Gianluigi Donnarumma in the second minute of injury time to give North Macedonia an incredible 1-0 victory.

Italy will again be absent from the World Cup in Qatar after also failing to qualify for the 2018 tournament in Russia when it lost in a playoff to Sweden.

That was a traumatic experience for a nation that had previously been to every tournament since 1958, and this failure is all the more remarkable given that it was crowned European champion less than nine months ago.

That success for Roberto Mancini's side came during a world record 37-game unbeaten run, but four draws in its last five qualifiers last autumn saw it finish second in its group to Switzerland, exposing it to the dangers of the playoffs again.

"It's hard to explain, it's such a huge disappointment," captain Giorgio Chiellini said to RAI.

"We've made mistakes since September and we've paid for them. We're distraught."

North Macedonia, the Balkan nation of just two million people, held Italy to a draw in Turin in 2018 World Cup qualifying and beat Germany away in this campaign before appearing at its debut European Championship in 2021.

"We won the Italian way against the Italians, a goal from just two shots," said their coach, Blagoja Milevski.

 

Penalty miss costs Turkey

The team will now go to Porto to face Portugal on Tuesday, after the Euro 2016 winner defeated Turkey 3-1 at the Estadio do Dragao, albeit only after Burak Yilmaz missed a crucial late penalty for the visitor.

The home side was cruising thanks to first-half goals by Brazilian-born midfielder Otavio and Liverpool forward Diogo Jota.

But Turkey's veteran skipper Yilmaz pulled a goal back in the 65th minute, setting up a tense finish.

Turkey was then awarded a late penalty when a foul on Enes Unal was detected following a VAR review, but Yilmaz put the spot-kick over the bar and Matheus Nunes secured Portugal's victory in stoppage time.

Turkey has not appeared at the World Cup since coming third in Japan and South Korea in 2002.

Portugal has not missed out on the tournament since 1998 and, at 37, Cristiano Ronaldo's dream of World Cup glory remains alive.

 

Bale brilliance

Meanwhile, Gareth Bale was in inspirational form as his brace secured a 2-1 win for Wales against Austria in Cardiff.

Bale has only played five times for his club Real Madrid this season, and just twice since August, but the Wales captain started at the Cardiff City Stadium and opened the scoring from a stunning 25th minute free kick.

He then struck again, with a superb hit across goalkeeper Heinz Lindner into the far corner, to double the lead six minutes after half-time.

Wales, bidding to qualify for its first World Cup since 1958, then held on after Austria reduced the deficit in the 64th minute when Marcel Sabitzer's shot deflected in off Ben Davies.

"I'll run myself into the ground for this country, we all did tonight," Bale, who came off right at the end with cramp, told Sky Sports.

Robert Page's team will be at home in the playoff final but must wait until at least June for that, with the ongoing war in Ukraine meaning its tie away to Scotland remains on hold for now.

Sweden set up a playoff final against Poland after an extra-time strike by Robin Quaison gave it a 1-0 win over the Czech Republic in Solna.

Quarterfinalist in 2018, Sweden got its winner in the 110th minute as Saudi Arabia-based Quaison finished after a one-two with Alexander Isak.

Poland received a bye to the play-off final after would-be opponent Russia was suspended from all international competition until further notice following the invasion of Ukraine.