Jose Canale scored on the first sudden death penalty kick, Orlando Gill made two key saves in the shootout, and Paraguay upset Germany 4-3 on penalties Monday to earn the biggest upset of the 2026 World Cup so far.

The round of 16 match ended 1-1 after extra time. Paraguay had gone in front when Julio Enciso scored on a header late in the first half. Kai Havertz equalized in the 52nd minute for four-time champion Germany.

Germany thought they had taken the lead in extra time when Jonathan Tah headed home from a corner in the 102nd minute. But after a lengthy VAR review, the goal was ruled out for a foul on Paraguary goalkeeper Gill by Waldemar Anton.

Gill appeared to go to ground easily and did get back on his feet by the time Tah got his head to the ball.

England great Alan Shearer said it was a “very, very soft.”

“Not for me, I don’t agree with that decision at all,” he said on BBC.

“He falls to the ground far too easy. Yes, there’s contact, but it’s a contact sport. There are 13 bodies in the six-yard box, not for me.

“I don’t agree with that. The ‘keeper buys it. Very, very soft, that is, very soft.”

In the shootout, Havertz’s opening spot kick was saved by Gill to give Paraguay the early advantage. When Woltemade’s attempt was saved, Paraguay needed to just make one of their next two penalty kicks to progress.

But they incredibly missed both to leave the shootout all square at 3-3 after five attempts.

Tah then stepped up and blasted his attempt horribly over the bar before Canale slotted home the winner.

“We had to analyze every player, every detail. Thanks to that I was able to only miss two penalties,” Gill said.

“This is for all the people of Paraguay.”

Speaking after the match, Havertz apologised to fans.

“I don’t have much to say. This is now my second World Cup and we’ve missed moving onto the next round twice now in a row. I want to apologise for that,” he said.

“We are all very disappointed. We had many plans for this year’s World Cup. It is not a very good feeling to disappoint again. The team tried a lot.”

Paraguay will next face the winner of Tuesday’s match between France and Sweden on July 4 in the round of 16 in Philadelphia. A win in that match would land them back in Foxborough for a quarterfinal match on July 9.

Germany had won six of seven penalty shootouts in major tournaments, including six straight since losing to Czechoslovakia in the 1976 European Championship final.

In the only previous World Cup match between the teams, Germany beat Paraguay 1-0 in the round of 16 at the 2002 tournament. Nearly a quarter-century later, Paraguay has its revenge.

Paraguay had appeared in five previous knockout games but failed to score in each. It advanced only once in those previous occasions, winning on penalty kicks against Japan in the round of 16 at the 2010 tournament in South Africa. It fell that year to eventual champion Spain in the quarterfinals.

Monday was Germany’s first knockout game since the 2014 final in Brazil when the Germans beat Argentina 1-0 to capture their fourth World Cup title.

Brazil late show sends Japan packing

Substitute Gabriel Martinelli has scored an added-time winner as Brazil snatched a place in the last 16 of the World Cup with a 2-1 win over Japan in Houston.

Carlo Ancelotti’s side were stunned when Japan took the lead with a superb strike from Kaishu Sano after 29 minutes, but replied when Casemiro atoned for a poor first-half performance with a fine header.

The game appeared to be heading towards extra time after a tense final period but Martinelli, sent on by Ancelotti on 66 minutes, capped the fightback after being played in by Bruno Guimaraes.

It was harsh on an obstinate Japan side, who were chasing their country’s first World Cup knockout win, but the five-time world champions finished strongly after a lethargic first-half display.

“We can never be content with what we’re doing,” Ancelotti said through a translator.

“We’re doing a good job. We are performing. But you can never be content because we want to play better. We want to play at the highest level.”

The South Americans found it difficult to create openings but did have an early chance as a Bruno Guimaraes shot was deflected behind and Matheus Cunha had an effort pushed wide by Zion Suzuki.

Sano, booked early on after catching Vinicius Junior late, escaped further punishment for a clumsy challenge on Cunha.

That was to prove controversial as the Mainz midfielder gave Asia’s top nation the lead just before the half-hour, seizeing on Danilo’s loose pass and powering past Casemiro before burying a low shot beyond Alisson Becker.

Brazil were reduced to tame long-range efforts from Vinicius and Cunha in response, but Ancelotti’s halftime adjustments prompted a change of tempo.

Guimaraes tested Suzuki with a strong header and Casemiro had an even better chance moments later, planting his header against Takehiro Tomiyasu on the line when he seemed certain to score.

Casemiro made no mistake when he got another chance on 56 minutes, heading past Suzuki at the back post from a Gabriel cross.

Vinicius almost put Brazil ahead when he weaved his way through and attempted to flick over Suzuki, but the keeper managed to touch on to the post.

Five minutes of added time had elapsed when Guimaraes slipped in Martinelli and he bent a shot past Suzuki.

“The gap between us is closing now,” Japan coach Hajime Moriyasu said through a translator.

“Brazil is a top-tier team and we’re definitely approaching that level.

“To win the title was our dream and our goal and we couldn’t achieve that ... I told them that I was really sorry that I was not good enough to lead them to that level to achieve that goal.”

Brazil will face either Ivory Coast or Norway in New Jersey in the last 16.

— with 7NEWS.com.au