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Morocco defeated the Netherlands in a penalty shoot-out to advance to the last 16 of the World cup on Monday after a thrilling battle in Monterrey finished 1-1 after extra-time.

Morocco goalkeeper Yassine Bounou made the crucial save to block the Netherlands’ fifth penalty from Crysencio Summerville before striker Ismael Saibari stepped up to blast home the winning spot-kick that sealed a 3-2 shootout win.

The victory sends Morocco into a last-16 clash with Canada in Houston on Saturday.

An enthralling match had gone to extra time after Issa Diop had glanced in a dramatic equaliser for Morocco in the first minute of stoppage time as the Netherlands closed in on victory.

The Dutch had taken the lead midway through the second half with a goal from Cody Gakpo, playing just days after his partner had confirmed the death of the couple’s unborn son.

Liverpool forward Gakpo sank to the turf and appeared overcome with emotion as he was surrounded by team-mates in a prolonged group embrace.

But Morocco forced extra time when an unmarked Diop headed home from substitute Chemsdine Talbi’s cross in injury time.

Morocco had created the better chances of a fractious encounter, which saw players from both sides flying into tackles to test the patience of Brazilian referee Wilton Sampaio.

The Atlas Lions almost took the lead on 20 minutes when Neil al-Aynaoui glanced an Achraf Hakimi corner goalwards only to be denied by a superb reflex save from Netherlands goalkeeper Bart Verbruggen.

Verbruggen was pressed into action moments later, this time doing well to tip a vicious strike from Hakimi over the bar.

The fierce nature of the contest was on full display midway through the half when Saibari was lucky to escape sanction after elbowing Jan Paul van Hecke in the face.

The Dutch continued to enjoy plenty of possession but were unable to convert it into goalscoring chances.

Their best effort came on 44 minutes when Tottenham’s Micky van de Ven uncorked a ferocious shot from the edge of the area that was tipped over by Bounou.

Van Hecke continued to find himself in the thick of the action, and after bloodying his head in a collision in the penalty area, made his presence felt with a crunching tackle that upended el-Aynaoui just before half-time.

As the half ended, Saibari just failed to connect with a cross that flashed across the Dutch goal before going behind.

The drama continued into an end-to-end second half, but appeared to have tilted in the Netherlands’ favour when coach Ronald Koeman brought on forward Wout Weghorst in a flurry of substitutions after the hydration break.

Weghorst made an immediate impact, flicking on a long ball to send Summerville bearing in on goal. Summerville crossed to Gakpo, who hurled himself at the ball to score.

The Netherlands, superbly marshalled by Gakpo’s Liverpool team-mate Virgil van Dijk, appeared to be heading for victory but Diop’s late header sent it to extra-time.

Morocco looked to have made the breakthrough when Soufiane Rahimi went through on goal in the 96th minute, only to be denied by a jaw-dropping save from Verbruggen.

The Netherlands held on for penalties, but despite Morocco missing their first when El-Aynaoui hit the bar, the North Africans recovered to win.

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Germany forward, Kai Havertz, has lamented his country’s elimination from the 2026 World Cup in the hands of Paraguay.

Havertz was one of the three players to miss a penalty, as they lost 4-3 in the shoot-out, after the match ended 1-1 in regulation time.

Julio Enciso opened the scoring in the last-32 fixture, before Havertz headed in the equalizer.

The Arsenal man stepped up for the first penalty kick and saw his effort saved comfortably.

Nick Woltemade’s effort was also saved, before Jonathan Tah blazed over.

I’m speechless. My second World Cup, and we’ve messed up for the second time,” Havertz told reporters.

“The last few tournaments were a disaster. The only thing I can say is I’m sorry.

“We players need to take a long, hard look at ourselves. We’re playing for a huge country with a rich football history.”

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Brazil national football team staged a dramatic second-half comeback to defeat Japan national football team 2-1, with Gabriel Martinelli scoring a stoppage-time winner to send the five-time world champions into the FIFA World Cup Round of 16.

Japan produced an impressive first-half display and stunned the Brazilians in the 29th minute through Kaishū Sano. The midfielder drove forward from the centre of the pitch before firing a low shot beyond goalkeeper Alisson Becker to hand his side a deserved lead.

Despite dominating possession before the break, Brazil struggled to break down Japan’s disciplined defence and went into half-time trailing 1-0.

Head coach Carlo Ancelotti responded by introducing Endrick, whose arrival injected greater pace and urgency into Brazil’s attack.

Japan goalkeeper Zion Suzuki produced several outstanding saves to preserve his side’s advantage, but Brazil eventually found the equaliser shortly before the hour mark.

Veteran midfielder Casemiro rose above the defence to power home a header from a cross delivered by Gabriel Magalhães, bringing Brazil back into the contest.

The equaliser completely shifted the momentum in Brazil’s favour as they pushed relentlessly for a winner.

Vinícius Júnior came agonisingly close after seeing a superb effort tipped onto the woodwork, while Japan gradually retreated under sustained pressure.

Just when the match appeared destined for extra time, Bruno Guimarães delivered a pinpoint pass to Martinelli at the far post.

The Arsenal forward kept his composure and curled a precise finish in off the upright in the 96th minute, completing Brazil’s comeback and securing a place in the knockout stage.

The victory keeps Brazil on course for a potential meeting with Argentina national football team later in the tournament, while Japan’s search for a first competitive victory over Brazil continues.

The result also marked Brazil’s first World Cup victory after trailing at half-time since defeating Turkey national football team on June 3, 2002.

Brazil also dominated possession throughout the contest, completing 682 passes, with Gabriel Magalhães attempting 135 passes—the highest by any Brazilian player at this year’s World Cup.

The South American giants will now face either Norway national football team or Ivory Coast national football team in the Round of 16 as they continue their pursuit of a record-extending sixth FIFA World Cup title.