No major international tournament is complete without the equal joy and despair that comes with a penalty shootout. Euro 2024 had its first taste of penalties last night, when Slovenia battled to a 0-0 draw with Portugal over the course of 120 minutes. Slovenia may even have considered themselves favorites, with keeper Jan Oblak saving a Cristiano Ronaldo penalty in the first half of extra time.

Slovenia just needed to surpass Portuguese keeper Diogo Costa. Incredibly, they didn’t manage this even once. Costa saved all three penalties he faced, and helped Portugal to the most one-sided shootout scoreline many of us have ever seen. It was a goalkeeping performance that will be remembered for generations.

It also provided the perfect excuse to flick back through footballing history and relive some of the best, and most iconic shootout performances ever.

Petr Cech vs Bayern Munich, Champions League Final 2012

Four years after John Terry’s infamous slip and shootout heartbreak against Manchester United in Moscow, Chelsea were back in the headline match of Europe’s biggest competition, this time against German giants Bayern Munich. Underperforming in the league, where they finished 6th, winning the Champions league was the only option for Chelsea if they were to return to the competition next season.

With the final being held at the Allianz Arena, Bayern’s home ground, Chelsea were well and truly up against it. Bayern held them in their own half virtually the entire game, and finally the pressure told, as Thomas Muller headed Munich in front with less than 10 minutes to go. But in the 88th minute, Didier Drogba, A.K.A Mr Cup Final, equalized with a bullet header to take the game to extra time.

But he quickly went from hero to zero, as he fouled Frank Ribery in the Chelsea box to concede a penalty. Arjen Robben, formerly of Chelsea, stepped up and absolutely belted it, but Petr Cech guessed right, and smothered the ball, keeping Chelsea’s dreams of a European trophy alive and forcing it to a shootout. Bayern took the lead after Manuel Neuer pawed away Juan Mata’s spot kick, and held that lead until the score was 3-2 after three penalties each. Cech had done his homework, going the right way for each penalty up to the point where Ivica Olic stepped up. Cech pushed his penalty wide, and the shootout was even again after Ashley Cole buried his strike into the corner.

Next up for Bayern was Bastien Schweinsteiger, to take them into sudden death territory. But his tamely struck effort was tipped onto the post by the big Czech, and Chelsea were a kick away from being European Champions. Drogba was elected to take it, to complete his redemption arc from Moscow four years previously, where he was sent off and unable to take a spot kick against United. He duly converted, and Chelsea had beaten Bayern in their own backyard.

Drogba may take the plaudits for his magnificent late header and winning penalty, but if you save three spot kicks on the biggest stage of all, you deserve equal if not extra credit. Cech was a Chelsea legend even by this stage, but his performance in Munich cemented his status as the Blues best keeper of all time.

Čech 2012 heroics 🔝#UCL pic.twitter.com/a38PgsIsEo

— UEFA Champions League (@ChampionsLeague) May 3, 2023

Helmuth Duckadam vs Barcelona, 1986 European Cup Final

Taking a real step back in history now, to a time when the Champions league didn’t exist. Instead it was called the European Cup, and it had no group stage. Instead, all 30 participating teams were placed into a tournament bracket, similar to the knockout stages of this year's Euros.

The 1985/86 edition saw a particularly surprising winner of the competition: Champions of Romania, Steaua Bucuresti. Beating Danish Vejle, Hungarian’s Honved, Finnish Kuusysi and Belgians Anderlecht on their way to the final, they faced Barcelona in the competition's centerpiece game.

Minnows Bucuresti forced Barcelona to penalties after the game finished 0-0 in normal time. What followed is surely one of the most bizarre shootouts in history. A total of eight spot kicks were taken, and 6 of these were saved. Bucuresti keeper Helmuth Duckadam saved all four of Barca’s attempts, brilliantly stopping three down to his right, and the winning save down to his left.

His spot kick heroics propelled Steaua Bucuresti their only European triumph in their history, and although they returned to the final in the 1988/89 season, they were unable to repeat the feat, Surely one of the most memorable, and bonkers, penalty shootouts of all time.

Iker Casillas vs Italy, Euro quarter final 2008

We all know how good Iker Casillas was in his prime. Golden glove winner, named in the FIFA world XI for 5 consecutive years between 2008 and 2012, and starting goalkeeper for Spanish juggernauts Real Madrid, he has a catalog of memorable saves and performances that would take a lifetime to watch through.

Arguably his most important performance came in the Euro 2008 quarter final with Italy, a game in which Spain dominated but couldn’t find that critical killer blow to break through the Azzurri’s backline. 0-0 after normal time and extra time, the game promised a dramatic shootout. Iker Casillas entered god mode and pulled out a mega performance, saving Italy’s second and fourth penalties from Daniele De Rossi and Antonio De Natale respectively, whilst also guessing correctly for the converted penalties taken by Fabio Grosso and Mauro Camoranesi.

In the semi final, Spain dispatched of Russia with a 3-0 demolition job, before scraping past Germany 1-0 in the final to bring home their first European crown since winning the same tournament in 1964, where they had beaten the Soviet Union in the final.

Casillas was awarded man of the match for his spot kick-saving display, but more importantly was a crucial factor in Spain's return to European top dogs, helping shape the international footballing landscape we know today.

Euro 2008 Quarter-Finals - Spain vs Italy

Casillas & Buffon 🧤 pic.twitter.com/XfmX58uRHf

— My Greatest 11 (@MyGreatest11) June 19, 2024

Tim Krul vs Costa Rica, World Cup 2014

Every football fan remembers this shootout. 2010 World Cup finalists the Netherlands were back in the quarter finals of the 2014 tournament hosted in Brazil, and faced off against the tournament’s sweethearts Costa Rica, who had magnificently topped group D over the likes of Uruguay, Italy and England.

Costa Rica had also been victorious in a penalty shootout in the previous round, where they had come through against Greece despite conceding an equalizer in the 92nd minute of normal time. So when the game against the Dutch finished 0-0 after 120 minutes, the Costa Ricans suddenly had their tails up, feeling they had the psychological edge in the shootout format.

Dutch manager Louis Van Gaal had made a seemingly bizarre substitution in the 120th minute, bringing on Newcastle goalkeeper Tim Krul, who hadn’t played a minute at the tournament thus far, in place of starting goalkeeper and Ajax number one Jasper Cillessen. However, there was method to the seemingly obvious madness. Tim Krul, knowing he wouldn’t receive many minutes in actual games, decided to specialize in penalties, researching all potential takers and their favorite shot placements.

Van Gaal himself has since said: “It’s a matter of thinking logically. Since you’re allowed to select three goalkeepers (for the tournament), then you ought to select one on the grounds that he has saved a lot of penalties.”

Krul proved his manager absolutely spot on. He employed every distraction tactic in the book: trash talking, walking across the 6 yard box, taking an age to reach the goal line to keep the taker waiting and confronting every taker that stepped forward, doing absolutely anything that may create an element of doubt. The giant Dutchman saved two out of five attempts, both low to his left, and guessed correctly for the other three in a performance that has gone down in history.

While he couldn’t repeat the trick in the semi finals against losing finalists Argentina, the Oranje fans will always remember him fondly for those seven minutes against Costa Rica.

Random Goalkeeper Fact of the Day (150): Netherlands' Tim Krul became the first goalkeeper to be brought on specifically for a penalty shoot-out when he replaced Jasper Cillessen during his side's quarter-final game against Costa Rica in the last minute of extra time in 2014. pic.twitter.com/eoIcbTSlDO

— GoaliesAreDifferent (@goalkeepersdiff) April 9, 2024

Manuel Neuer vs Real Madrid, Champions League Semi Final 2012

Prior to their heartbreaking penalty defeat in their own ground against Chelsea in the final, Bayern had tasted penalty success in the previous round against a Jose Mourinho led Real Madrid.

After the first leg at the Allianz had finished with Bayern 2-1 up, the Germans traveled to the Santiago Bernabeu with just 90 minutes between them and a home Champions League final. Things couldn’t have possibly started worse, as Ronaldo slotted away an early penalty and then just eight minutes later, buried a 1v1. Bayern were 2-0 down inside 15 minutes, and with the aggregate score at 3-2 Madrid, they now had 75 minutes to find a goal. It duly arrived 13 minutes later when Bayern won a penalty of their own, this time converted by Arjen Robben.

The scoring was all done in the first half hour of the game, and while both sides continued to craft openings, countless saves by Neuer and Casillas kept the aggregate scoreline level.

Penalties arrived, Mourinho was confident, saying afterwards: “Cristiano (Ronaldo) and Kaka, they were two of the best penalty takers of the last decade. Honestly, when I got into this one (penalty shootout), I thought ‘come on, we are going to win this one.’”

Both Ronaldo and Kaka were Madrid’s first two takers, and both saw the penalties headed for the bottom left corner brilliantly, and almost identically saved by Manuel Neuer. Saving two penalties in a shootout is quite the achievement in itself, but to save spot kicks from two Ballon D’or winners back to back is unheard of.

Munich held their nerve, and in the end it was Bastien Schweinsteiger who put away the decisive penalty, ensuring Munich would have home advantage in the Champions League final. Whilst in the end they couldn’t make that advantage count, Neuer proved his credentials that night as one of the best keepers in the world, a title he still somehow competes for to this day.

saving penalty-kicks from two former Ballon d'Or winners , leaving one of the best managers oat in disbelief , and denying one of greatest teams in history the UCL.
He was too cold. https://t.co/M3v9X2LnOO pic.twitter.com/JXi3jnKe7g

— Stop That Neuer (@Goatkeeper1_) July 28, 2023

Oliver Kahn vs Valencia, Champions League Final 2001

I don’t think there will ever be another Champions League final quite like this one. Of course it involves Bayern Munich again (they love a penalty or two don’t they), and penalty drama absolutely dominated the course of the match, with three being awarded in normal time alone.

Both sides had received wickedly tricky knockout draws, with Bayern needing to overcome Manchester United and Real Madrid, while Valencia had to navigate all English knockout ties against Arsenal and surprise package Leeds United.

In the final, the first goal came inside three minutes, as Gaizka Mendieta converted a penalty past the stretching Khan after a handball by an off-balance Patrik Andersson. However, Munich responded positively and won a penalty of their own just five minutes later after Stefan Effenberg was barged over on the left side of the box. Mehmet Scholl took on the responsibility of taking the spot kick, but Valencia and Spain keeper Santiago Canizares smartly diverted the ball over the bar with his legs.

Still Bayern kept coming, and five minutes into the second half, they were awarded their second penalty, this time after a handball by Amedeo Carboni. Effenberg stood over the ball, desperate to avenge the missed penalty he had won earlier, and converted it, dragging Bayern back level.

Surprisingly, no further penalties were awarded, and a lack of clear openings meant the score remained 1-1 after extra time.

Bayern kicked first, but Paulo Sergio skied the penalty horribly. Khan was then sent the wrong way by earlier scorer Mendieta, and Valencia already had the upper hand after just two kicks of the ball.

But Kahn remained focused and unfazed, and dragged his side back into it when he acrobatically dived to his right to deny Zlatko Zahovic. Canizares saved the following penalty, diving on a poor penalty from Anderssen, and the pressure was back on Kahn. Carboni, who gave away Bayern’s second penalty, tried to outwit the German, going high down the middle. But Kahn, who had dived to his left early, stuck out a strong right hand to superbly divert it onto the bar to bring the shootout level once again.

The shootout entered sudden death from that point onwards, and five consecutive penalties were converted before the responsibility fell to Valencia center back Mauricio Pellegrino. He gave himself thinking time with a long run up, and leathered the ball towards the top corner. Khan, guessing correctly, got two strong palms behind the ball and somehow diverted it wide, winning Bayern Munich the Champions League for the first time since 1976, and avenging the anguish of their defeat in the previous years final to a dramatic late Manchester United comeback.

It is said you have to be a bit mad to be a goalkeeper, and Khan looked almost unhinged in the shootout, getting in his opposition ear to unnerve him, and making aggressive gestures and faces to put them off their stride. Whatever he did, it worked wonders and brought European glory back to Germany, and it shows that while goalkeepers suffer through mistakes, blunders and low points, criticized more than in any other position on the pitch, it pays to do your homework, and to be the hero of a shootout is why they put themselves through it all.