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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READ: ‘He did the most audacious piece of skill’ – Ronaldo’s early days at Man Utd

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While 55,000 fans enjoyed the first-half…