Worst penalty ever? Man Utd and Real Madrid’s disastrous shootout in 2017


Manchester United have been pretty terrible at penalty shootouts in recent years.

In fact, with the exception of victory over Rochdale during the 2019/20 season, the Red Devils have lost every single shootout that they’ve competed in since the 2009 League Cup final. Yeh, seriously.

United were dumped out of the FA Cup semi-finals in the same way just months later, before Chelsea compounded their misery ahead of the 2009/10 season by winning the Community Shield on penalties.

Man Utd’s awful shootout record

Then, David Moyes saw his team crash out of the League Cup against Sunderland from 12 yards, before Louis van Gaal witnessed the same misery in the same competition with Middlesbrough as the opponents.

Jose Mourinho also got a taste of the curse as United came up short against Derby County, before Ole Gunnar Solskjaer felt the pain too when David de Gea lost his nerve in the 2021 Europa League final.

Throw in last season’s FA Cup exit at the hands of Middlesbrough and it’s fair to say that Erik ten Hag could do a lot worse than making sure that his players practice the living daylights out of penalties.

Man Utd vs Real Madrid in 2017

However, without a doubt the worst shootout that United has ever contributed to actually came during pre-season with some even claiming that it’s the worst series of penalties of all time.

And as the Red Devils gear up for their latest set of pre-season friendlies, we couldn’t resist throwing it back to their 2017 clash with Real Madrid where everything turned to chaos from 12 yards.

Having drawn 1-1 with Los Blancos in the International Champions Cup courtesy of goals from Jesse Lingard and Casemiro, the heavyweight clash in Santa Clara, California, had to be settled by football’s favorite lottery.

Man Utd's De Gea celebrates.
Soccer Football – Real Madrid vs Manchester United – International Champions Cup – Santa Clara, USA – July 23, 2017 Manchester United’s David De Gea celebrates after saving a penalty kick REUTERS/Alan Greth

“The worst ever penalty shootout”

The result? Truly mind-boggling scenes in which just three (!!!) of the ten penalties were scored and even one of those, sheepishly converted by Luismi Quezada, barely found the back of the net.

That’s not to mention the fact that many of the seven misfires ranked among some of the most embarrassing we’ve ever seen with Victor Lindelof’s pitiful effort straight down the middle proving especially miserable.


Chuck in Anthony Martial, Theo Hernandez and Casemiro not even hitting the target and you quickly see exactly why the shootout gained its ‘worst ever’ tag. Be sure to check it out for yourself down below:

We have no words. What on earth was going on there?

A penalty-taking catastrophe

As much as it’s the tired old cliché of an armchair fan to say: “how can they not kick a football when they’re on that much money?” it does actually feel pretty pertinent for once when you watch that back.

Until Henrikh Mkhitaryan actually brings some skill to the equation by stopping the rot of four consecutive penalty misses, you’re forgiving for thinking that it was a case of the most spectacular miss wins.

And of all the infinitely strange shenanigans that can come with pre-season penalty shootouts from goalkeepers lining up and stupid celebrations, this might just take the cake as the silliest case of all.

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I’ve never felt so good about my own penalty-taking, let’s put it like that.

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