Italy missed out on the World Cup finals again after losing 1-0 at home to North Macedonia in their playoff semi-final on Thursday as Aleksandar Trajkovski's last-gasp strike earned the visitors a famous win.
European champions Italy did not qualify for the World Cup four years ago, their first failure to reach soccer's global showpiece tournament since 1958, but they dominated from the off in Palermo and looked on course for victory.
The hosts became more desperate in their search for a winner after the break as chances continued to come and go before, in stoppage time, Trajkovski arrowed in a stunning winner to spark wild North Macedonian celebrations.
Roberto Mancini's Italy side had 32 efforts at goal in the match, but somehow fell short, with North Macedonia going on to play Portugal in the playoff final next week for a place in the Qatar World Cup which will not involve Italy once more.
"It is a huge disappointment," Italy midfielder Jorginho told Rai Sport.
"It hurts, it hurts so much.
"We have always created and dominated matches but we have not been able to finish teams off. It is not to blame anyone in particular but it is the reality.
"I don't know why we haven't been able to do this, I am also involved in this, and it hurts me to think about it."
Without veteran pairing Leonardo Bonucci and Giorgio Chiellini through injury, Italy's makeshift defence was barely troubled in the first half, as all the action took place down the other end.
Domenico Berardi had the best of the openings having been presented with the ball after North Macedonia goalkeeper Stole Dimitrievski misplaced a pass, but the Sassuolo forward's shot was tame, with Dimitrievski getting back to make the save.
Ciro Immobile also wasted a glorious first-half chance for Italy when blazing over the bar from a good position.
Berardi was again guilty of profligacy after the break, shooting over when he should have hit the target.
As the match wore on, Italy nerves kicked in and their finishing became more erratic. Mancini shuffled his pack, giving Cagliari striker Joao Pedro his debut, but with their only meaningful attack of the match, North Macedonia seized their chance.
Italy did not look to be in too much danger, but Trajkovski, who plays in Saudi Arabia for Al-Fayha, had other ideas, writing his name into North Macedonian folklore with a shot that crept inside the post to stun the home fans.
Portugal survive late drama to beat Turkey in World Cup playoff semi
Portugal survived a nervy finale to move one step closer to reaching the World Cup with a 3-1 win over Turkey, who missed a late penalty that could have forced extra time in their playoff semi-final on Thursday.
Roared on by a sold-out Dragao Stadium in Porto, Portugal dominated the game from the start and went 2-0 up in the first half after Otavio scored one goal and created another for Diogo Jota.
But Fernando Santos's side were pegged back by a Burak Yilmaz goal in 65th minute that put the Portuguese fans on the edge of their seats as Turkey started to threaten.
Defender Jose Fonte then fouled Enes Unal inside the area in the 85th minute to concede a penalty but Yilmaz fired his effort high over the bar.
Portugal substitute Matheus Nunes then relieved the pressure on the hosts in added time with their third goal from a counter attack.
"I wasn't upset with the team but we played with fire today," Santos told reporters.
"We had the game under control but slowed down. Obviously the players are not machines, we didn't manage to score for 3-0 and those things can happen in football. But I'm glad we reacted very well. That moment (the penalty) could have been difficult for us."
After missing out on automatic qualification in November, Portugal will now host North Macedonia on Tuesday with the winner qualifying for the 2022 World Cup in Qatar.
Portugal would have been expecting to face Italy, but they were shocked in a 1-0 defeat to North Macedonia in the other semi-final in Palermo, depriving fans of a highly anticipated face-off between the last two European champions.
Portugal started strongly, scoring twice in the first half with the result looking like a foregone conclusion going into the break.
Brazilian-born Porto midfielder Otavio, a surprise inclusion in the starting team, provided Portugal’s main attacking threat.
He scored from a rebound in the 15th minute after a Bernardo Silva shot came back off the post and just before halftime, he crossed from the right flank for Jota to aim an unstoppable header into the net.
But Portugal took their foot off the gas in the second half and allowed the visitors to get into the game.
Yilmaz scored following a one-two with Cengiz Under and had the chance to equalise from the spot after the video assistant referee spotted a foul in the penalty area, but sent his effort soaring high over the bar.
Brilliant Bale inspires Wales to victory in World Cup playoff semi
Gareth Bale scored both goals as Wales edged Austria 2-1 in their playoff semi-final on Thursday to move a step closer to a first World Cup finals appearance in 64 years.
The 32-year-old forward fired home a precise free kick in the 25th minute to open the scoring, emphasising his role as the team's talisman with a superb effort in Cardiff.
It was followed up by quick thinking from a short corner in the 51st from which captain Bale scored again to ensure Wales’ progress to a playoff final at home to either Scotland or Ukraine in June.
A deflected shot from Marcel Sabitzer in the 64th minute offered Austria hope of a comeback as a wasteful Wales endured a nervy finish but the home side held on for a deserved win to stay on course for only their second World Cup appearance.
Bale lifted the atmosphere and propelled his team mates to victory with a superb left-footed free kick from outside the penalty area that dipped dramatically into the top corner of Heinz Lindner’s goal.
Wales, World Cup quarter-finalists in 1958, survived a scare when Christoph Baumgartner slammed the ball against the bar in the fifth minute but once Bale had opened the scoring they found their rhythm and created numerous chances.
Their pressing and counter-attacking game offered opportunities, especially five minutes from halftime when Aaron Ramsey sprinted upfield only to see his shot expertly turned around the corner by a diving Lindner.
The Austrian also made two important second-half stops from breakaways led by Dan James but could do nothing about Bale’s close-range shot that doubled the lead six minutes into the second half.
A short corner routine saw the ball played into the box where Ben Davies looked to bring it under control but Bale stole it off his team mate, turning to slam the ball home.
Real Madrid forward Bale should have had a hat-trick on the counter-attack just past the hour mark but his left-footed effort sailed wide.
Austria reduced the Wales lead when Sabitzer was given time to shoot from outside the area with the effort deflecting off Davies and wrong-footing goalkeeper Wayne Hennessey.
It threatened to make Wales pay for squandering their chances but they held out and might have added a third right at the end when Lindner made another fine stop to deny Ramsey.
"It was a massive game. We knew how big the game was, and we had to perform," Bale said.
"It was nice to see the free kick go in, to get some momentum. The second one was nice as well. I had some cramp at the end but I’ll run into the ground for this country."
Quaison fires Sweden to extra-time World Cup playoff win over Czechs
Sweden substitute Robin Quaison struck in the second half of extra time to secure a 1-0 win over the Czech Republic and set up a clash away to Poland next Tuesday with a place at the World Cup finals in Qatar up for grabs.
The Czechs had an early goal ruled out for a foul and the Swedes had the lion's share of possession for most of the playoff semi-final, but the two sides struggled to break each other down in a game full of tough tackling and wayward passing.
Alexander Isak almost opened the scoring early with a deft volley form a corner that flew just wide, and winger Emil Forsberg had a shot deflected past the post just before halftime as Sweden tried to take the game to the Czechs.
The attacking trio of Forsberg, Isak and Dejan Kulusevski caused the injury-hit Czechs all manner of problems but, with the Swedes missing both of their first-choice full backs, they often struggled to get the ball to their forwards out wide.
The visitors had some dangerous moments of their own, with Tomas Soucek flashing a header just wide on the hour and Jan Kuchta wasting a decent chance by curling a shot past the left post when he should at least have forced a save by Robin Olsen.
Sweden substitute Mattias Svanberg went closest for the Swedes in normal time, but his header from Forsberg's corner was aimed straight at visiting goalkeeper Tomas Vaclik.
The game finished scoreless after 90 minutes and appeared to be heading for penalties when Quaison danced through the defence before exchanging passes with Isak and slotting the ball into the net to send the home fans in the 48,628 crowd into ecstasy.
There was still time for 19-year-old Anthony Elanga to win his first cap and the young winger did his bit, holding up the ball and showing flashes of his electric pace as the Swedes ran down the clock.
"I'm just glad we scored a goal, I'm very happy right now," Sweden captain Victor Lindelof said.
"We still managed to create some chances and it felt like we were stronger than them.
"The first half was OK, I don't think we were prepared for their duels and the way they played, but in the second we came out a better team and played better football," he added.
Uruguay, Ecuador qualify for World Cup finals in Qatar
Uruguay and Ecuador secured their spots at the World Cup finals on Thursday, joining Brazil and Argentina as the automatic qualifiers from the South American group.
Uruguay beat Peru 1-0 and Ecuador lost 3-1 to Paraguay, meaning both teams have 25 points with one match to play. Peru are on 21 points in fifth place.
Peru, Colombia (20 points) and Chile (19) will now vie for fifth place and a playoff spot against a team from the Asian confederation.
Peru host Paraguay, Colombia travel to Venezuela and Chile are at home against Uruguay on Tuesday in the final round of games.
Uruguay earned the win over Peru thanks to Giorgian de Arrascaeta's goal three minutes before half time. Peru were adamant a late looping shot held by Uruguay keeper Sergio Rochet had crossed the line but the referee waved away their claims for an equaliser.
Peru's defeat meant Ecuador qualified regardless of their result in Paraguay and they were overrun by the home side, who gave coach Guillermo Barros Schelotto his first win since he took over in October last year.
Robert Morales put Paraguay ahead after 10 minutes and Piero Hincapie put through his own goal on the stroke of half time to give the hosts a 2-0 lead at the break.
Miguel Almiron made it 3-0 nine minutes into the second half before Jordy Caicedo scored for Ecuador with five minutes left. It was Paraguay's first win in eight games.
Also on Thursday, Brazil beat Chile 4-0 at the Maracana stadium, with the aid of two penalties from Neymar and Philippe Coutinho.
Vinicius Junior got his first international goal and substitute Richarlison completed the scoring in stoppage time.
Colombia hit the net for the first time in eight games in a 3-0 victory at home to Bolivia, Luis Diaz, Miguel Borja and Mateus Uribe getting the goals.
Argentina take on Venezuela in Buenos Aires on Friday.
Ten-man Canada fail to clinch World Cup spot with loss to Costa Rica
Battling Costa Rica edged 10-man Canada 1-0 on Thursday to deny the North Americans their first chance to clinch a spot in the 2022 World Cup finals.
Canada arrived in San Jose unbeaten in the final round of CONCACAF qualifying and looking to secure a berth in their first World Cup finals since 1986.
In little more than a half hour, though, they found themselves down 10 men and things went from bad to worse when Celso Borges netted a first half stoppage-time header that proved the only goal of the game.
Despite the loss, Canada sit top of the group standings on 25 points, three points clear of Mexico and the United States who battled to 0-0 draw at Azteca Stadium. With the win, Costa Rica moved into fourth on 19 points, still in the hunt for automatic qualification.
The top three automatically earn spots in November's World Cup in Qatar with the fourth-place finisher facing an Oceania team in an intercontinental playoff for another berth.
Canada's next chance to end their 36-year World Cup finals wait comes when they host Jamaica on Sunday in Toronto, before wrapping up qualifying on Wednesday away to Panama.
Despite their group rivals gaining ground, Herdman was confident Canada would advance.
"We're not looking over our shouder, destiny is in our hands," he added.
"We'll get to Qatar."
They'll hope for a better start than in San Jose, where they were reduced to 10 men in the 34th minute when Mark-Anthony Kaye picked up a second yellow card.
Borges superb header put the Ticos in front, but they faced a more disciplined, regrouped Canada in the second half as the visitors applied all the pressure. Tajon Buchanan hit the crossbar and Richie Laryea's long-range drive forced a diving save out of Keylor Navas.
In Panama, the home side needed a victory over winless Honduras to try to scrap their way into the top three. But they were forced to settle for a 1-1 draw when a Kevin Lopez 65th minute header cancelled out Rolando Blackburn's first half strike.
The draw dropped Panama into fifth, a point behind Costa Rica, but still in the chase for a spot in Qatar with two games remaining.
In Kingston, El Salvador saw their hopes of getting to the finals end with a 1-1 draw with Jamaica.
Needing a win to keep alive any chance of sealing fourth place and a playoff, El Salvador started brightly, going ahead in the 21st minute with Eriq Zavaleta heading home from a corner.
But Jamaica, already eliminated, struck back to crush El Salvador dreams with a 72nd minute equaliser from Andre Gray.
Japan, Saudi Arabia seal World Cup spots as Mitoma downs Australia
Japan's qualification for a seventh straight World Cup finals was secured by substitute Kaoru Mitoma's late double on Thursday as the Samurai Blue beat Australia 2-0 in Sydney to ensure Saudi Arabia also qualified for this year's tournament in Qatar.
Mitoma replaced Takumi Minamino in the 84th minute and claimed a quick-fire brace that guaranteed Hajime Moriyasu's side a top-two finish in Group B of Asia's preliminaries and sealed Saudi Arabia's World Cup spot.
Australia cannot finish higher than third and will play the third-placed finishers in Group A in a playoff, with the winners facing the fifth-best South American side for a World Cup spot.
Mitoma was the difference between the teams at the Olympic Stadium as the winger, on loan at Belgian side Union SG from Brighton & Hove Albion, struck twice in five minutes.
The 89th-minute opener came after Mitoma linked up with his former Kawasaki Frontale team mates Hidemasa Morita and Miki Yamane before slotting past goalkeeper Mat Ryan.
The second came four minutes into stoppage time as Ryan allowed Mitoma's low shot to slip through his grasp.
Saudi Arabia took to the field in Sharjah knowing they had already secured World Cup qualification and played out a 1-1 draw with China.
Saleh Al Shehri put Herve Renard's team in front in first half injury time, only for an 82nd minute penalty by Zhu Chenjie to earn China a point.
That result moved the second-placed Saudis to 20 points in Group B, one behind Japan with one round of matches remaining. Australia are third, six points adrift of the Japanese.
In Group A, Son Heung-min opened the scoring as South Korea moved to the top of Group A with a 2-0 win over Iran. Both teams had already secured their places at the finals in Qatar.
The Tottenham Hotspur forward put Paulo Bento's side in front with a shot from distance in first-half stoppage time at the Seoul World Cup Stadium and defender Kim Young-gwon slotted home the second 21 minutes into the second half.
The Koreans have 23 points and lead Iran by a point with the United Arab Emirates still in third on nine points following their 1-0 loss against Iraq in Riyadh.
Hussein Ali scored eight minutes into the second half to move the Iraqis into fourth, a point behind the UAE, and keep alive their hopes of facing the Australians on June 7.
Lebanon missed the opportunity to move into third as they slumped to a 3-0 loss against Syria in Sidon.
First-half goals from Alaa Al Dali, Mardik Mardikian and Mohammad Al Marmour earned Syria their first win of this round of qualifiers and dealt Lebanon's World Cup chances a potentially fatal blow.