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5 Worst Penalties in Football History

There is nothing more anxiety-inducing than taking a penalty in the world of football. It’s a gilt-edged chance to score – and you’re expected to do so. Miss, and ignomy reigns.

Today, we’ll look at five instances where players got their penalty kicks completely wrong – here are the five worst penalties in football history.

We had plenty to choose from, so we’d like to add a couple of dishonourable mentions. Robert Pires’ baffling effort against Manchester City needs a mention, as does Ademola Lookman’s pathetic panenka for Fulham in 2021.

Brahim Diaz vs Senegal

This one should be very fresh in your mind. Brahim Diaz was trusted with taking a spot kick in the final few seconds of the game between Morocco and Senegal in the AFCON 2025 final – instead of burying it, Diaz chipped the ball right into the hands of the grateful Edouard Mendy.

In Diaz’s defence, he had an awfully long wait before he took the penalty, as Senegal head coach Pape Thiaw had ordered his players off the pitch in protest at the decision.

Nevertheless, Diaz opted to try and end the game with a floruish – instead, the Real Madrid man got it completely wrong and Senegal eventually won the trophy in extra time.

John Terry vs Manchester United

Chelsea fans, avert your gaze. There have been some disasters at Stamford Bridge since John Terry missed his penalty in the shoot-out of the 2008 Champions League final against Manchester United, but none of them stung quite as deeply as this.

Despite being a defender, as captain, Terry stepped up to take Chelsea’s fourth penalty of the shoot-out. Just before he struck the ball, his standing foot gave way – leading him to slip and put the ball well over the crossbar.

United eventually won the shoot-out – the Blues would have to wait another four years before they secured their first Champions League trophy.

Steve Simonsen vs Huddersfield Town

This is perhaps the most obscure entry on our list, but it carried all the weight in the world for Sheffield United and Huddersfield Town fans in the 2011/12 League One Playoff final.

During a lengthy penalty shoot-out, all the outfield players had taken their penalties. It was now down to the goalkeepers – Town ‘keeper Alex Smithies put his spot kick away, but Blades shot-stopper Steve Simonsen could not repeat the feat.

Choosing power over placement, Simonsen blasted the ball over the bar, crushing United’s promotion hopes in an instant and condemning them to another season in League One.

Simone Zaza vs Germany

We don’t usually engage in schadenfreude, but this one was just too funny to avoid laughing at. It took place in the quarter-finals of Euro 2016, when Italy took on Germany.

After a cagey, if exciting game of football, the game went to a penalty shoot-out. There were plenty of missed spot-kicks throughout, but none of them were squandered quite as spectacularly as Simone Zaza’s.

Zaza began by making a comedically unorthodox run-up – he appeared to be hopping around on hot coals, rather than steeling himself to take a penalty. Then, when he connected, the ball ballooned several feet over the bar to send Italy out of the competition – the memes still haven’t stopped.

Roberto Baggio vs Brazil

Roberto Baggio is one of the greatest strikers of all time. Sadly, this penalty dominates his legacy – it left a lasting impression on his career that he was never able to shake off.

We chose this as our worst-ever penalty due to the context – if Baggio missed, Italy’s World Cup dreams were over. And he did.

Leaning back, Baggio hit the ball over the crossbar. He remained stationary for several seconds, distraught at his error – this moment immortalised Baggio in infamy as the ‘man who died standing’.

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