What is the longest penalty shootout in football history? Penalty shootouts are one of the most breathtaking moments in football, where the line between glory and defeat is just one shot away. Throughout the history of the king sport, the "longest penalty shootout in football history" has created strange and unforgettable stories, from the perseverance of amateur teams to dramatic nights on the big stage. Matches like Villarreal 11-10 Manchester United in the 2021 Europa League final or penalty shootouts that lasted up to dozens of shots have become symbols of the determination and intense emotions that football brings. Let's take a look at the top 10 longest penalty shootouts in football history with Wintips through the following article!
What is the longest penalty shootout in football history?
10. Villarreal 11-10 Manchester United (22 penalties)
The 2021 Europa League final was a bitter memory for Manchester United goalkeeper David de Gea. Throughout the penalty shootout, De Gea failed to save any of the 11 penalties that Villarreal's players accurately took. The climax of the disappointment came when he stepped up to take the decisive penalty but was saved by goalkeeper Geronimo Rulli, ending a nightmare evening.
Rulli's save not only ended United's title hopes but also sent Villarreal to the top of Europe with the first major trophy in the club's history. Meanwhile, this defeat was a huge shock for De Gea and the Old Trafford team, as they could only watch their opponents celebrate in sweet victory.
9. Macclesfield Town 11-10 Forest Green Rovers (24 penalties)
In 2001, Macclesfield Town and Forest Green Rovers faced off in the first round of the FA Cup, a game that started with the usual routine of the long-standing competition. However, things quickly escalated into a dramatic affair as the match lasted over three and a half hours, including extra time and an incredible 24-shot shootout.
In this nerve-wracking encounter, the pressure was on every player, but in the end, the composure of Kevin Langan and Lee Glover made the difference. Langan scored with a decisive strike, while Glover finished the game with a cool finish, giving Macclesfield a dramatic win. The result set them up for the next round, where they would face Swansea City.
The match was not only a physical and mental challenge but also a living testament to the unpredictable appeal of football, where special moments can turn ordinary matches into history.
8. Brockenhurst 15-14 Andover Town (30 penalties)
In the Hampshire Senior Cup, the match between Brockenhurst and Andover Town became an unforgettable match, recorded in the history of English football thanks to its unbelievable drama. After the two teams could not determine the winner in the regular time and extra time, the match was forced into a penalty shootout, where each kick became a test of spirit and accuracy.
A record was set when both teams took 30 consecutive penalties, an unprecedented number in the history of penalty shootouts in England. In this tense match, players from both sides showed nerves of steel as they took turns to successfully complete their kicks. However, luck was not on Andover Town's side in the end when they missed the decisive penalty, handing Brockenhurst a thrilling victory.
This historic moment is not only a testament to the players' determination and bravery, but also highlights the appeal of football, where anything unexpected can happen.
7. Olympiacos 15-14 AEK Athens (30 penalties)
The Greek Cup final between Olympiacos and AEK Athens saw a thrilling encounter, marking one of the most dramatic matches in the history of Greek football. The two top Greek teams put on a spectacular show, ending 120 minutes of regulation time and extra time with a 4-4 draw. That was enough to satisfy the audience, but what happened next really turned this match into a legend.
Both teams entered the penalty shootout, where the nerves and mettle of each player were tested to the limit. A total of 29 penalties were taken, with only one missed. In the end, the decisive moment belonged to veteran Olympiacos goalkeeper Antonis Nikopolidis, nicknamed “Silver Fox”. He not only saved the decisive kick but also brought his team to the championship in an emotional way.
This match was not only a great match but also engraved in history as a symbol of sportsmanship and the boundless drama of football.
6. Liverpool 14-13 Middlesbrough (30 penalties)
In 2014, in a tense Carabao Cup (then known as the Capital One Cup) match, Middlesbrough produced an unforgettable encounter with Brendan Rodgers' Liverpool. After 90 minutes of regulation time, Middlesbrough were leading, but Liverpool refused to give up hope. The decisive moment came in injury time, when Middlesbrough's Patrick Bamford scored an equaliser for the visitors, taking the match into extra time.
All eyes were on the penalty shootout, where each kick became a test of the players' mettle. Finally, after 30 penalties, something unexpected happened. Middlesbrough's Albert Adomah, in a breathless moment, missed the crucial penalty, giving Liverpool the win. It was a dramatic penalty shootout, with the decisive kicks making for one of the most memorable matches in Capital One Cup history.
5. Scunthorpe United 14-13 Worcester City (32 penalties)
While the shootout between Middlesbrough and Liverpool was dramatic, it was not the longest in English football that year. The real prize for 'longest' goes to the FA Cup tie between Scunthorpe United and Worcester City, where the two teams took a total of 32 penalties, setting a record for the most in the competition's history. The game became a real battle of nerves, with each kick potentially deciding the fate of the team.
In the tense shootout, Scunthorpe striker Miguel Llera was unlucky to miss his first penalty, leaving the home fans worried. However, Llera rallied and scored the winner with the next kick, after Worcester's Wayne Thomas had saved Llera's earlier effort. The victory not only brought joy to Scunthorpe but also created one of the most memorable moments in FA Cup history.
4. Netherlands U21 13-12 England U21 (32 penalties)
Long penalty shootouts aren't the only thing that happens in senior football, but they can also be dramatic at youth level. Back in 2007, at the European Under-21 Championship, England U21 had a tense encounter with Netherlands U21. After a 1-1 draw in regulation time and extra time, the two teams were forced to go into a penalty shootout to decide the winner.
Although it was a long shootout with plenty of tension, the decisive moment came from Anton Ferdinand. In a dramatic moment, Ferdinand hit the crossbar, officially eliminating England U21 from the tournament. This match has become a memorable one for England fans, as they witnessed a crucial defeat, despite many shots being taken beforehand.
3. Old Wulfrunians 19-18 Lane Head (44 penalties)
The match between Old Wulfrunians and Lane Head in the JW Hunt Cup produced one of the strangest and most dramatic penalty shootouts in the history of English football, especially in amateur football. After a 3-3 draw after extra time, the two teams entered a tense, drawn-out penalty shootout that eventually became the longest of its kind. It was a battle of nerves and composure, where each kick could decide the fate of the team.
An interesting detail in this match was the decisive kick from Old Wulfrunians left-back Jack Marsh. More importantly, Jack Marsh was not only a player but also a teacher by profession and the son of the club secretary, Simon. His decisive kick sealed the victory for his side, creating an iconic moment in a match filled with the drama and surprises that only amateur football can deliver.
2. KK Palace 17-16 Civics (48 penalties)
We move on to Namibia, a country famous for its wildlife, diamonds and… endless penalty shootouts in the 2005 Nations Cup final. It was a thrilling game, not only because of the tension but also because of the staggering number of 48 penalties taken. However, if you pay close attention, you will notice that only 33 goals were scored, as 15 of the penalties were either missed or poorly taken.
So the question is: how could there be 48 penalties and only 33 goals scored? The simple answer is the lack of accuracy in the penalty shootout. Still, in terms of total penalties, the match remains the second longest penalty shootout in history, with a remarkable record for its length and bizarreness in football.
1. Washington 25-24 Bedlington (54 penalties)
Finally, the title of the longest penalty shootout in football history goes to two non-league clubs in the North East of England. The match took place in the Ernest Armstrong Memorial Cup last year, with just 40 fans in attendance to witness the clash between Washington and Bedlington. While the crowd may have seemed small, those who were present certainly had an unforgettable experience from a game full of drama and surprises.
The match lasted so long that it required 54 penalties to decide the winner, breaking the previous record set in Africa nearly two decades earlier. More than just a penalty shootout, this was a battle of nerves and precision, with each kick potentially changing the outcome of the match. The tension was not only on the field but also the joy and excitement of those witnessing a legendary match with a record that surpassed all limits.
Conclusion
The longest penalty shootouts in football history are a testament to the drama and intense emotions that this sport brings. From the 54-kick match between Washington and Bedlington to other famous shootouts, each kick is not only a test of technique but also a mental challenge for the players. Such moments go beyond winning or losing, etching themselves into the memories of fans and writing unique pages in football history. In a sport that is inherently full of surprises, the longest penalty shootouts always remind us that every match can become legendary.
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