An August 7, 2003 file photo shows Portuguese Sporting Lisbon soccer player Cristiano Ronaldo during a soccer match at the new Alvalade stadium. Manchester United invested in their future strike power by signing the 18-year-old Ronaldo from Sporting Lisbon for 12.24 million pounds ($19.60 million).

When Cristiano Ronaldo gave O’Shea ‘a migraine’ in his Man Utd audition

As the old saying goes, you’ll never get a second chance to make a great first impression.

On August 6, 2003, Manchester United agreed to play a pre-season friendly against Sporting Lisbon at the opening of the Estadio Jose Alvalade.

Sporting were the reigning Portuguese champions and had several talented players in their squad. None more so than a young Cristiano Ronaldo, who was regarded as the next big thing in Portugal.

But Ronaldo had only made his senior debut a year earlier and was still a relatively unknown teenager outside of his homeland, with just five professional goals to his name.

The winger was originally meant to be on the bench against United, only for Ricardo Quaresma to swap Lisbon for Barcelona a week before the game. While Quaresma may not have lived up to expectations at Camp Nou, that transfer had huge ramifications for the future of European football. His spot in the line-up against United was given to Ronaldo, who was soon following Quaresma out of the door.

“I was his coach when he played against Manchester United,” former Sporting manager Fernando Santos said in 2016. “I put him in the team and now I regret it.”

Apart from a brief cameo appearance against Inter Milan, this was Ronaldo’s first real test against one of Europe’s biggest clubs. The world was watching, and he was ready to put on a show.

Wearing the No.28 on his back, Ronaldo quickly acquainted himself with United’s back four and went through his now famous repertoire of stepovers. The then-18-year-old displayed confidence and an arrogant swagger that belied his age, fearlessly taking on senior internationals at any given opportunity. 

He seemed to pay particular attention to a hapless John O’Shea, effortlessly skipping past the right-back and making him look like a cone on a training pitch. Ronaldo’s deadly combination of dazzling footwork and terrifying speed turned O’Shea inside and then out, leaving him with a “look of pain and bewilderment across his face”, as Sir Alex Ferguson put it in his 2013 autobiography.

The winger had quickly transformed Sporting’s new stadium into his own playground.

United, who had won all four of their previous pre-season friendlies, clearly weren’t prepared for what awaited them in Lisbon and found themselves 1-0 down at half-time.

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Cristiano Ronaldo

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While 55,000 fans enjoyed the first-half entertainment, O’Shea probably wishes that he’d just stayed on the team bus. The defender later claimed that he was jet-lagged following United’s pre-season tour in America, but even a fully refreshed Cafu wouldn’t have stopped Ronaldo in this kind of form.

Inside the Estadio Jose Alvalade, Ferguson famously told Peter Kenyon that Ronaldo had given O’Shea a “bloody migraine”, but the Republic of Ireland international was subjected to even more merciless taunts from his own team-mates.

“I played and it’s a funny story because John O’Shea played right-back against him and we didn’t know who Ronaldo was,” Rio Ferdinand told Copa’s YouTube channel in 2020.

“We missed out on signing Ronaldinho so we were a bit deflated at the time. So we get in at half-time and John O’Shea must have had an oxygen tank next to him. He was in bits. We said, ‘Sheasy, get close to him!’ And he just couldn’t even answer us.”

Writing in his autobiography, former United captain Roy Keane said: “I saw how good Ronaldo was that day. He was up against John O’Shea. Sheasy ended up seeing the doctor at half-time because he was actually having dizzy spells.”

Like a bloodthirsty animal, Ronaldo refused to take pity on his prey and continued to torment O’Shea in the opening stages of the second half.

With 53 minutes on the clock, a weary-looking O’Shea was spared any more punishment and substitute Mark Lynch now had the unenviable task of marking Ronaldo.

Lynch, who scored an own goal on his only competitive appearance for United, unsurprisingly suffered a similar fate to his predecessor in the right-back position.

Despite trying to properly introduce Ronaldo to English football with some rough challenges, Lynch was ultimately left chasing shadows.

“Ronaldo struck fear into me,” Lynch told Bleacher Report in 2017. “You had to watch him so carefully, and at one point, he put the ball through my legs, and all I could do was bring him down. They scored their second goal from that free-kick. He was unplayable that night.”

We can only imagine that Lynch’s struggles made O’Shea turn to his team-mates, pointing out that defending against Ronaldo is far easier said than done.

Lynch was then given some respite when Ronaldo decided to showcase his versatility, switching to the right flank and running at Danny Pugh instead. He ran rings around a bewildered Pugh and then moved into midfield, sending Phil Neville to the shops with some brilliant footwork in the closing stages.

Sporting won the game 3-1 but, more importantly, Ronaldo had passed his audition with flying colours. If people didn’t know about him beforehand, they certainly did after the full-time whistle. 

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Manchester United's Cristiano Ronaldo scoring a header against Roma, Stadio Olimpico, Rome, 04 April 2007

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The United players were unaware that a potential deal had already been discussed and spoke to Ferguson in the dressing room, urging him to sign the teenager who had put them on their backsides.

Originally, United had looked at potentially loaning Ronaldo back to Portugal for another season, but that performance made them realise that he was ready for Premier League football.

“The first game that I played against Manchester United was an unbelievable game. It was the perfect night, the perfect night,” Ronaldo told Sky Sports in 2016. “After the game, some of my team-mates said, ‘Listen, you’re going to go to Manchester, trust me!’

“Sir Alex Ferguson was there, and [they said] he wants to speak with you. I go to the dressing room, he introduced me to the players. For me, I was a little bit shy. And Sir Alex Ferguson said to me, ‘Listen, I want you now.'”

After selling David Beckham to Real Madrid and missing out on Ronaldinho, Ferguson certainly wasn’t going to let Ronaldo slip through his fingers. The United squad had to sit on a bus outside the stadium for an hour after the game as the respective hierarchies of the two clubs accelerated their negotiations.

Five days later, the deal was official.

United agreed to pay a £12million fee to secure his services, temporarily making Ronaldo the most expensive teenager in British football history.

“Ronaldo bumped into John O’Shea, and John joked, ‘You owe me for getting you this move!'” Danny Pugh told Bleacher Report in 2017. “It was translated for him, and Ronaldo began laughing a lot.”

Ten days after that game in Lisbon, Ronaldo made his United debut against BoltonIt was the first of Ronaldo’s 292 appearances in his first spell at the club, during which time he scored 118 goals and won three Premier League titles, the Champions League, an FA Cup, two League Cups and the Club World Cup. 

While Ronaldo’s arrival was the start of a brilliant period for United, we can’t help but think about O’Shea. After all, he must have needed to bring a pack of paracetamol to every training session until Ronaldo’s departure in 2009.

By Nathan Egerton

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