It was on this day 51 years ago that the first ever penalty shoot out arrived in the English game as Manchester United and Hull city battled it out in a semi-final of the Watney Cup. This meant that the first man to take a penalty in England was George Best, with the dubious distinction of the first miss going to the great Dennis Law. 

The game took place two years after an Israeli man, Yosef Dagan, having watching his nation get knocked out of the 1968 Olympics with the drawing of lots, first formally proposed the modern shoot out. From 1970 they took hold and spread all over the world and remains one of the most fiercely debated aspects of the game. 

But for all the drama and heartbreak, the psychological battle of the penalty shoot out has given rise to some truly great moments. Moments that condense all that is good about the game into a neat five second segment as a player conquers their nerves to outwit a helpless keeper. And sometimes the hapless striker literally fall flat on their face. 

Here’s ten times penalties went about as well and as poorly as can possibly be imagined.





Ezequiel Calvente 



Scored in an under 19’s clash between Spain and Italy back in July 2010, Ezequiel Calvente’s penalty picked up quite a lot of attention at the time and so it should. In a world of pointless backflip goals scored against Sunday league keepers Calvente’s technique had some genuine merit, even if the risk of failure was so high. As the Spaniard reached the end of his run up he swung his right boot back and start to bring it forward in a motion that he was going to shoot to the left hand side of the goal only to stab it with his standing foot into the opposite corner. 


Cruyff pass 



For many people Johan Cruyff’s 1982 penalty against Helmond Sport introduced the concept that you could do anything but shoot at a penalty kick. Indeed when Henry and Pires failed to replicate the technique or Messi and Suarez successfully executed, Cruyff’s name was the one recalled. Interestingly, however, there are two examples that pre-date Cruyff by a quarter of a century. First came this (hyperlink the this with link 1 below), similar but not identical, effort from Northern Ireland and then Belgium’s Rik Coppens executed the technique perfectly (hyperlink with 2) in a game against the Netherlands which could well be where a then 10 year old Cruyff got his inspiration.


Kevin Pressman vs Wolves



For the sake of actually being able to see what’s going on we’ve had to use a clip that’s commentary is so remarkably underwhelming that it damn near detracts from the fact that you are watching an English goalkeeper of the 90’s scoring possibly the greatest penalty of all time. But really, what a hit son.


Vidal vs AC Milan



The technique on this penalty from Arturo Vidal back in 2013 is pretty astonishing. Using his instep he hammers the ball straight into the top corner of the AC Milan goal. It’s hard to pin down exactly what we love so much about this one, it’s just so deliberate. There’s no notion of him just lashing across the ball and sending it into the roof, he new exactly where it was going.




Watch the video here.


We know you’ve seen this before but Inventing a new way to take a penalty when you are stepping up to win your nation its first ever European Championship is definitely the coolest thing anyone has done on a football pitch.




Pilo (Sao Paolo)



It’s not that we’ve never seen a player slip when attempting a penalty before, but it’s hard to imagine anyone getting it more wrong than Sao Paolo’s, Pilo. His connection is so poor that he somehow manages to send the ball backwards. An impressive feat of incoordination at any level, let alone in top tier professional football.


Amir Sayoud



Truly awful. During a Algerian league game, Amir Sayoud attempted to throw the keeper by stuttering his run up, only to end up face down with his limp shot trickling towards goal. He also managed to pick up a booking for illegally coming to a complete stop in the course of taking the penalty.





While still playing for Bordeaux in his native France in a 1989 a young Eric Cantona hit a Panenka so terrible it didn’t even reach the line. It was so slow that his momentum meant that he practically caught up with it, unable to do anything but watch as the keeper scrambled over from the other side of the goal to collect. 


Peter Devine 



You’ve gotta do something pretty special to be remembered for a moment that took place in a 1991 HFS Northern Premier League Division One Cup final, but that’s exactly what Peter Devine did. He can blame a truly terrible looking surface for causing his first stumble but from there we’re afraid it’s all on Peter as he elects to continue going, take a wild swing and injure himself in the process.





The hubris is almost too much to bear in this November 2019 effort. With the penalties tied at 4-4 and a chance to win the Copa Verde Final, Paysandu’s Oliveira starts his painfully slow shuffle towards the ball. 14 seconds later he stops just shy, takes a step back and shanks it wide.


Words by Andy Gallagher





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