5 Times Cristiano Ronaldo Ended on the Losing Side in Penalty Shootouts Before Al Nassr’s Heartbreaking Loss to Al Ain

The AFC Champions League dream is over for Cristiano Ronaldo and Al Nassr. Following a narrow loss in the opening RO16 leg against Al Ain, Luis Castro and his team fought back to tie the game on aggregate with a 4-3 win in the return leg. However, their hopes were crushed in the penalty shootout as the UAE-based side emerged victorious with a 3-1 win. Though it may seem strange to watch Ronaldo’s team struggle with penalties, it makes one wonder about earlier situations in which the Portuguese superstar has lost in shootouts. Well, here are five instances for you. 

1) Arsenal vs Manchester United: 2005 FA Cup final 

Cristiano Ronaldo’s first defeat in a penalty shootout came on May 21, 2005, during the FA Cup final against Arsenal. While the Gunners came with a 3-0 win over Blackburn Rovers, the Red Devils booked their place in the finals after a 1–4 victory over Newcastle United. Unfortunately, even after the extra time, neither side could find goals at the Millennium Stadium, with the match going to penalties. 

The first three penalties were successfully converted by both sides, with a young Ronaldo even finding the net for United. However, Paul Scholes missed the fourth one, and Ruud van Nistelrooy’s fifth strike was in vain as Arsene Wenger’s side triumphed over Sir Alex Ferguson and Co. with a 5-4 score, securing their 10th FA Cup.

2) Real Madrid vs Bayern Munich: 2012 UEFA Champions League 

April 26, 2012, was the first and only time Cristiano Ronaldo lost the penalty shootout with Real Madrid. Although Jupp Heynckes’ Bayern Munich clinched a 1-2 victory in the opening semi-final leg, Jose Mourinho’s side managed to make a comeback in Leg 2 at Santiago Bernabeu with a 2-1 win. Thanks to a brace from CR7 and no goals in extra time, the match went to penalties with a 3-3 aggregate scoreline. 

However, Los Blancos couldn’t progress to the finals as they lost 1-3 on penalties. The saddest part was that Ronaldo even missed the spot-kick for his side as Real Madrid’s attempt to win their 10th coveted trophy failed, extending their UCL final exile to 10 years since their last victory in 2001/02. 

3) Portugal vs Spain: UEFA EURO 2012

The penalty shootout curse followed Cristiano Ronaldo in the Euros as well. After defeating the Czech Republic in the QFs, Portugal met 2010 World Cup winners Spain in the SFs on June 27, 2012. Neither side could find a winner as the knockout round went to penalties.

Unfortunately, not only did Os Navegadores miss 2 penalties through Joao Moutinho and Bruno Alves, but Ronaldo didn’t even get his chance to take the 5th penalty as Vicente del Bosque’s side won the shootout 2-4. The rest was history, as Spain successfully managed to extend their dominance by winning the 2012 Euro, defeating Italy 4-0 in the finals. 

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4) Portugal vs Chile: 2017 Confederations Cup 

2016’s Euro winner, Portugal was eligible to play in the FIFA Confederations Cup, which used to be held every four years. It used to include the champions from each of the six Continental Championships, including the UEFA, CONCACAF, CONMEBOL, CAF, AFC, and OFC, as well as the WC holders and the host country. 

For the 10th and final edition, besides Cristiano Ronaldo’s nation, Germany, Chile, New Zealand, Cameroon, Australia, Mexico, and the host nation, Russia, participated. Portugal’s journey came to an end in the semi-finals against Chile on June 28, 2017. After a stalemate, Fernando Santos’ side suffered a 0-3 defeat in the penalty shootout against the 2015 Copa America winners, with Ronaldo again missing out on the opportunity to take the final penalty.

5) Manchester United vs Middlesbrough: FA Cup 2022

Before the Al Ain one, his last defeat in the penalty shootout came during his 2nd spell at Manchester United. Ralf Rangnick’s side hosted Middlesbrough at Old Trafford to play in the FA Cup 4th round on February 5, 2022. In the first half, Cristiano Ronaldo failed to convert from the spot, which would have put the Red Devils in front. Although Jadon Sancho came to the rescue, the Englishman’s strike went in vain as Matt Crooks equalized to take the match to extra time. 

With no turning point in extra time, the match went to penalties. Every penalty found the net until Anthony Elanga missed his at Stretford End, concluding the shootout with a score of 8:9. Chris Wilder’s side successfully managed to end Ronaldo’s FA Cup hopes with United. 

The recent loss to Al Nassr against Al Ain is Cristiano Ronaldo’s sixth defeat in penalty shootouts throughout his illustrious career. Nevertheless, soccer is an unpredictable sport, and anything is possible. For now, CR7 must try to get over the unfortunate defeat and come back stronger than ever. 

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