Top 12 longest penalty shootouts in football history

Penalties are always dramatic but these shootouts increased the heartbeat of fans significantly.

The world of football has witnessed several highly engaging ends to the matches which bring excitement to the fans and can end up being worse if their side is on the losing end. When the scores are level in extra time, the penalty shootout determines the winner of the match. It is a fair way of determining the winner, which can sometimes seem unfair with the effort the team put in. 

It is worth noting that many dramas have occurred in recent years, such as the Washington-Bedlington game, where the sides took 54 penalties. In the Europa League final of 2021, Rulli was the ultimate hero after taking a penalty between two goalkeepers and saving De Gea’s penalty to score the winning goal. 

Now, Let’s take a look at the top 12 longest penalty shootout in football history

12. Macclesfield 11-10 Forest Green: 22 Penalties

It was a first-round FA Cup match between Macclesfield and Forest Green. After the initial score was drawn, a penalty shootout determined the winner between the two sides. There were 22 spot kicks taken by both sides, but ultimately, Lee Glover won the match for Macclesfield. 

11. Villarreal 11-10 Manchester United: 22 Penalties

After defeating Arsenal and AS Roma in the semis, Villarreal and Manchester United reached the final of the Europa League 2021. A penalty shootout determined the winner of the tournament after a 1-1 match. All 22 players scored penalties, but ultimately it was Villarreal’s keeper Rulli and De Gea who decided the winner. However, De Gea was unable to stop Rulli from saving his effort after he saw his effort saved. 

10. Brockenhurst 15-14 Andover Town: 30 Penalties

After a goalless draw between Brockenhurst and Andover Town in the Hampshire Senior Cup, a penalty shootout determined the match. As a result of a historic win, Brockenhurst progressed to the next round after a penalty shootout in which 30 spot kicks were taken by the two teams. 

9. Olympiacos 15-14 AEK Athens: 30 Penalties

The biggest teams in the Greek league, Olympiacos and AEK Athens set up a thrilling Greek Cup finale. The match was a classic encounter between the two top sides in the country, as there was drama and intense rivalry. With the score tied at 4-4, both sides took 30 penalties, 15 each. However, AEK Athens missed the last penalty and Olympiacos won. 

8. Liverpool 14-13 Middlesbrough: 30 Penalties

This match, in which Middlesbrough fought hard against Brander Roger’s Liverpool, would not be forgotten. Liverpool were just a whisker away from winning the match, but Patrick Bamford scored a goal in extra time to even the game. There was then a penalty drama, where Boros missed the last penalty, handing Liverpool the victory after 30 spot kicks. 

7. Worcester 13-14 Scunthorpe: 32 Penalties

The FA Cup’s longest penalty shootout ever took place between Scunthorpe and Worcester, where 32 penalties were taken in total. As a result, Scunthorpe won the tie after Worcester missed at the end, moving on to the next round. 

6. Netherlands U21 13-12 England U21: 32 Penalties

The European U21 championship where the future stars represented their nation to make a name for themselves. The Netherlands and England faced off in the semi-finals. The Dutch, however, won after England missed the last kick, which enabled them to score the winner and advance to the final. 

5. Preston 16-15 Fulham: 34 Penalties

Another of the records was set this year, in 2024. Premier League team Fulham were stunned in this high-drama penalty shootout of the EFL Cup (Carabao Cup).

4. Old Wulfrunians 19-18 Lane Head: 44 Penalties

The JW Hunt Cup was contested between two non-league sides Old Wulfrunians and Lane Head. A total of 44 penalties were taken between the sides in which Old Wulfrunians came victorious after a series of penalties. After a lengthy period of prolonged shootout, Lane Head missed the final spot kick, resulting in Old Wulfrunians winning. 

3. KK Palace 17-16 The Civics: 48 Penalties

This shoutout took place in the 2005 Namibian Cup final when both sides headed into a penalty after the score was tied at 2-2. KK Palace won the cup after 48 penalties were taken between the sides. KK Palace won the trophy after Civics missed the spot kick at the end, making this one of the longest penalty shootouts in history. 

2. Washington 25-24 Bedlington: 54 Penalties

A penalty shootout took place after the first round Memorial Cup game ended 3-3 after extra time. Both sides took 54 penalties between them in the second-longest penalty shootout in football history. In the end, Washington advanced to the next round in the Cup by winning the tie on penalties. 

1.  SC Dimona 23-22 Shimshon Tel Aviv: 56 penalties

The latest record was set in May of 2024. Imagine taking that many penalties to decide a winner. This game was for the semi-final promotion play-off between SC Dimona and Shimshon Tel Aviv.

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