5 players who have missed the most penalties in the 21st century

Even Messi and Ronaldo have not managed to convert all of their penalty kicks
Even Messi and Ronaldo have not managed to convert all of their penalty kicks

In hindsight, a penalty seems to be the easiest way to get on the scoresheet. Beating only the keeper from 12 yards out can be considered a walk in the park, especially for the top goalscorers in the world.

However, when you factor in the weight of expectations and the brilliance of goalkeepers, the situation becomes a lot dicier.

Even the best in the business have failed to convert from the spot, time and again; and this list will only drive the point home.

Here are the top five players who have missed the most penalties this century:


#5 Antonio Di Natale - 14 penalties missed

Udinese Calcio v Atalanta BC - TIM Cup
Udinese Calcio v Atalanta BC - TIM Cup

Udinese legend Antonio Di Natale flew under the radar for most of his professional career. Unlike most strikers of his generation, Di Natale did not grab the headlines when he was a teen. The centre-forward took his time and only came on his own after turning 30.

He had a mighty right foot, possessed impressive off-the-ball movements, and had a knack for being in the right place at the right time. To top it off, he was exceptionally loyal to Udinese and rejected offers from other top Serie A clubs multiple times in his career.

Di Natale scored 191 goals for Udinese in the Italian top-flight, becoming the club’s record goalscorer. Di Natale is also the sixth-highest goalscorer in the history of Serie A.

The former Italy international took 55 penalties in his career, scoring 41 and missing 14. He retired from football in the summer of 2016.


#4 Zlatan Ibrahimovic - 16 penalties missed

AC Milan v SSC Napoli - Serie A
AC Milan v SSC Napoli - Serie A

Love him or hate him, there is no way of ignoring the enigmatic and undoubtedly entertaining presence of Zlatan Ibrahimovic. The Swedish sharpshooter has plied his trade at many top clubs in Europe and continues to dominate the field to this day with AC Milan.

He is currently the only 40-year-old striker to play for a top-drawer European club and features regularly. The Swede has made 11 appearances for Milan so far this season, scoring seven goals.

Outrageously arrogant interviews aside, Zlatan Ibrahimovic brings a lot more to the table. He is an excellent striker of the ball, can win aerial and ground duels with ease, and is often surprisingly unselfish in the final third.

Being in his 40’s, he does not go for many acrobatic goals these days, but he has scored quite a few in his illustrious career.

As you would expect, Zlatan has always been the primary spot-kick taker for his teams. Over the course of his career, he has taken 100 penalties, scoring 84 of those.

#3 Francesco Totti - 18 penalties missed

AC Chievo Verona v AS Roma - Serie A
AC Chievo Verona v AS Roma - Serie A

In football, loyalty has become a rare commodity. Footballers do vouch to remain faithful to their clubs but tend to look for greener pastures after the slightest of conflicts.

AS Roma legend Francesco Totti has been a glowing exception to this norm in the 21st century. He never held the club hostage and stayed put despite getting multiple offers from some of the most prestigious clubs in Europe, including Real Madrid.

For over 20 years, he was one of the first names on the team sheet for AS Roma. Naturally a second-striker, Totti had a knack for drifting into little pockets of space, unlocking defenses with little one-twos. He made 618 Serie A appearances for Roma, scoring 250 goals.

During his time with Roma, he was the team’s primary spot-kick taker. He took 95 penalties in the 21st century, converting 77 of them.


#2 Cristiano Ronaldo - 28 penalties missed

Norwich City v Manchester United - Premier League
Norwich City v Manchester United - Premier League

Manchester United forward Cristiano Ronaldo has been a phenomenon since making his first-team debut for Sporting Lisbon in 2003. The mercurial Portuguese has played for Manchester United, Real Madrid and Juventus, scoring goals and reaching new milestones for fun wherever he goes.

Cristiano Ronaldo’s best goalscoring spell came during his time with La Liga giants Real Madrid. Between 2009 and 2018, the Portugal skipper scored 451 goals for the club, helping them to two La Liga titles and four Champions Leagues, among other honors.

For his exploits, he won four Ballons d’Or while wearing the famous white jersey of Real Madrid.

To no one’s surprise, Cristiano Ronaldo has been the first-choice penalty taker for each of his clubs. So far, the generation’s leading goalscorer has taken 171 penalties for his clubs and country, finding the back of the net a total of 143 times.

Also take a look into Cristiano's Net Worth 2021


#1 Lionel Messi - 29 penalties missed

Argentina v Uruguay - FIFA World Cup 2022 Qatar Qualifier
Argentina v Uruguay - FIFA World Cup 2022 Qatar Qualifier

Paris Saint-Germain forward Lionel Messi is arguably the best player the world has ever seen. He is an exceptional goalscorer, a magnificent creator, and has always managed to lead by example on the football pitch.

Before his highly-controversial move to PSG in the summer of 2021, Messi had only played for Barcelona. The Argentine was at the club for 21 long years, first graduating from La Masia then emerging as the best of the generation.

Messi made 772 appearances for Barcelona in his career, registering 672 goals and 301 assists. His exploits at the Camp Nou saw him win six Ballons d’Or. He won his seventh Ballon d’Or at PSG in the last week of November.

To date, Messi has taken 132 penalties, scoring 103 times.

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