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Cristiano Ronaldo was left in tears as his quest for a first goal at Euro 2024 saw the Portugal captain denied from the penalty spot by Slovenia goalkeeper Jan Oblak, before Roberto Martinez's side won the resulting shootout to set up a quarter-final clash against France.
Portugal had a golden chance to take the lead in the last-16 tie during extra time but surrendered the chance as Ronaldo's penalty was agonisingly saved by the Atletico Madrid shot-stopper.
A frustrating evening saw Ronaldo desperately try to score, with his spot-kick effort in extra-time forcing a stunning save from Oblak who tipped the shot onto the post.
Ronaldo was unable to keep his emotions in check after being denied and burst into tears as Portugal manager Martinez rallied his squad for a team talk.
His mother, Maria, was also seen crying in the stands as she watched on helplessly and unable to offer her superstar son any comfort or words of encouragement.
Cristiano Ronaldo broke down in tears after missing a penalty against Slovenia in the Euro 2024 last-16 tie
Ronaldo's quest for a first goal at Euro 2024 saw the Portugal captain denied from the penalty spot by Slovenia goalkeeper Jan Oblak
Oblak made a superb dive to tip Ronaldo's powerful penalty onto the post in extra time
The 39-year-old sobbed uncontrollably as he was consoled by team-mates after his miss as the former Euro 2016 champions attempted to rally for the second-half of extra-time.
His penalty would have put Portugal in a strong position to win the match as they tried to take the lead in the dying minutes of the game, with Ronaldo confidently stepping up to shoot having previously scored past Oblak at club level.
The legend was later reprieved as Ronaldo confidently scored Portugal's first penalty during the shootout after the match ended goalless following extra time.
Ronaldo confidently showed his composure by smashing his shot into the corner past a diving Oblak, with Portugal goalkeeper Diogo Costa the real hero as he saved every Slovenia attempt.
The initial spot-kick that left Ronaldo in floods of tears was prompted after Liverpool winger Diogo Jota was fouled in the box to give the former Real Madrid, Man United and Juventus star an opportunity from 12 yards that many expected him to convert.
Ronaldo had previously only missed 29 of his 192 career penalties, with Monday marking his first failure since being denied in Man United's FA Cup penalty shootout against Middlesbrough in 2022.
The Al-Nassr striker couldn't contain his emotions as the referee blew for the break following Ronaldo's sensational miss and broke down in tears in what will no doubt go down as iconic scenes.
Portugal stars surrounded Ronaldo and attempted to calm him down knowing their Euro 2024 destiny was on the line.
Swathes of Portugal team-mates rallied around Ronaldo as he continued to cry after missing his penalty
Ronaldo scored on his second attempt against Oblak as Portugal won the penalty shootout
Man United full-back Diogo Dalot was on-hand to console Ronaldo and pulled him aside while uttering words of comfort and trying to help the team captain regain composure.
Gary Lineker was shocked to see the legendary player in such a state and referenced his famous words to England manager Bobby Robson after Paul Gascoigne broke down in tears in the 1990 World Cup semi-final, saying: 'Look at the tears that followed and at this point somebody needed to have a word with him.'
Micah Richards also commented on Ronaldo's situation and heaped praise on Dalot for pulling his former Man United team-mate to one side during the crisis moment.
'Dalot. Dalot there. Shows his passion for the game there. He's absolutely devastated but he's got a chance to put it right,' he said.
Ronaldo was a mess as he continued to cry fearing Portugal's Euro 2024 journey could be over
Ronaldo was later reprieved as Portugal beat Slovenia during the penalty shootout to advance to the Euro 2024 quarter-finals
Fans and critics on social media were quick to pounce on Ronaldo's missed effort and subsequent outpouring of emotion, with one post on X stating: 'Ronaldo miss the penalty. He has let his country down.'
Another added: 'Ronaldo crying. I can't take this,' alongside several broken heart emojis.
A third comment sought to poke fun at the Portuguese's misfortunes, posting: 'Ronaldo Crying haha what a cry baby.'
Ronaldo is now tasked with leading Portugal to a Euro 2024 semi-final when they take on France in a replay of the 2016 final.