England's Ashley Cole, front, tussles with Portugal's Cristiano Ronaldo during the Euro 2004 quarter final soccer match between England and Portugal at the Luz Stadium in Lisbon, Portugal, Thursday June 24, 2004.

‘My toughest opponent’: The TWO times Ashley Cole pocketed CR7

As the Premier League celebrated its 30th anniversary in the summer of 2022, the BBC conducted a vote on the competition’s greatest-ever XI. Some positions invited more debate than others, but there was little doubt over Ashley Cole’s inclusion at left-back.

Just as unsurprisingly was Cristiano Ronaldo’s name on the right side of attack. The Portuguese forward reached levels seldom seen in the English game as Manchester United claimed three titles in successive years between 2006 and 2009.

He was English football’s record departure and remains the last Premier League player to claim the Ballon d’Or.

So – long before Pep Guardiola imported ‘Juego de Position’, where a football match more closely resembled a series of one-on-one battles – Cole vs Ronaldo was appointment viewing.

Two players so great that they transcended the eras they played in facing off against one another. Few, if any, winger vs full-back duels have been quite so compelling.

“Over the years I had some great battles with Ashley Cole, he does not give you a second to breathe,” Ronaldo later reminisced of the toughest defenders he faced.

“He was such a tenacious player when he was at his peak, quick, tough in the tackle. You knew it would never be an easy game.”

Cole, giving a hint of who tended to get the better of their battles, actually named Messi as the most difficult to deal with forward he faced.

“It has to be Messi,” he told Jamie Carragher on an episode of Monday Night Football in 2019.

“People talk about Ronaldo more because I played against him more. But I think to mark Messi, on his day… he was just too good for me. But, again, he’s never scored [against me],”

Perhaps the greatest testament to Cole’s quality was from Carlo Ancelotti, who was aghast at the left-back’s omission from the 2010 Ballon d’Or shortlist.

“Everyone can see that Ashley Cole is the best left-back in the world,” the then-Chelsea boss said.

“Every year it is difficult for a defender to be on the list for the Ballon d’Or because usually it is just for strikers and midfielders.

“In his career [Paolo] Maldini deserved to win the award but the only reason he didn’t was that he was a defender. [Cole] played with extraordinary quality for us last season, both defensively and when scoring goals and making assists.

“And he can run for much more than 90 minutes: he is a light man, his weight is 65 kilos, and his endurance is really fantastic – he is like the great Sebastian Coe. Cole and Maldini are different players because they have different bodies and different skills but professionally and in terms of personality they are the same. They have the same passion for the job.”

Comparisons to Paolo Maldini don’t come lightly, not least from a man that played alongside and later coached the legendary Italian defender.

But on his day Cole was that good. And there are no better illustrations of that than two of his career-defining performances, up against Ronaldo, for club and country.

Euro 2004

Cole had faced off against Ronaldo once before – in a full-blooded Premier League classic that would forever become known as the Battle of Old Trafford.

There were no fewer than 31 fouls and eight yellow cards, including two for Patrick Vieira. It was a goalless draw, but an early marker as Arsene Wenger’s Gunners came away from Manchester with a valuable point.

An 18-year-old Ronaldo had only been signed by United a month prior. It was only his third Premier League start and first real experience of the blood and thunder his new surroundings offered.

Arsenal, of course, ended that Premier League season unbeaten, while Cole was absent for the return fixture at Highbury and the FA Cup semi-final defeat to United at Villa Park.

Ronaldo’s debut season in England had featured glimpses of his prodigious talent but lacked consistent end product, with just four goals and four assists for Sir Alex Ferguson’s side.

That first year in England is epitomised by a dizzying feint that left Cole on his arse in that first appearance against Arsenal while ultimately failing to find a breakthrough.

Still, he’d shown more than enough to nail down a spot in Luiz Felipe Scolari’s favoured XI as Portugal hosted Euro 2004.

In round two, as England faced off against Portugal in the quarter-finals, it was Cole who came out on top.

The hosts broke England’s hearts by emerging victorious in the penalty shootout, but Cole won his own battle, shutting out Ronaldo in a performance that’s since been lionised as one of the greatest individual displays.

“Can’t defend? Cole was England’s rock, making a superb double block from Ronaldo early on and saving England on numerous occasions, including a goal-line clearance in extra-time,” was the man-of-the-match verdict in the BBC’s player ratings.

Chelsea 2006

Over the following years, Ronaldo began to refine his game, transforming from a rough diamond into a polished gem. Ferguson’s men did the league double over Arsenal in the 2004-05 season and he scored twice – while Cole notched an own goal – in a 4-2 victory at Old Trafford in February.

But it wasn’t until the 2006-07 campaign that he truly flourished into a fully-fledged world-beater, United’s top scorer as they claimed their first league title in four years.

Jose Mourinho’s Chelsea had just been enjoying their imperial era, conceding just 37 goals as they claimed back-to-back titles. Then they signed the best left-back in the country.

They failed to maintain those standards, but Cole’s first Chelsea appearance at Old Trafford suggested he’d be the perfect addition.

Just as he had that evening at the Estadio da Luz, Cole produced a near-perfect performance with the perfect blend of physicality and tenacity to shut out his opposite number, who was increasingly becoming United’s talisman.

“I was so focused on that game. Even in the changing room I just felt different going into this game,” Cole later recalled in an interview with ChelseaTV.

“My focus and concentration – mentally I was on it. I came to show him the line a lot because I kind of fancied my chances up against him with my pace. And a little bit of mentality actually, I think I got in his head a few times. He always wanted that extra trick.

“I gave him a strong tackle, maybe it was a foul or not, I don’t know. And I felt at that time he didn’t want it no more. He’s kind of put his hand up and said, ‘I wanna go off.’ So I think it was a good time to say I had him in my pocket.

“But I had so much respect for him, it was always a tough battle against not just Manchester United but against him.

“And to see what he’s gone on to do is testament to how good he actually was. This is just one of my good moments against him and I would probably say I came out on top on this occasion.”

It wasn’t the only time. And that’s the true mark of Cole’s quality.

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