Ashley Cole was Cristiano Ronaldo’s most difficult opponent – the pair treated fans to epic battles.
That’s the view of Arsenal legend Martin Keown, who believes the Manchester United icon developed a fixation on his ex-teammate.
While Ronaldo is now an established striker, he was a tricky right winger during his first spell at United in the Premier League – which saw him directly go up against left-back Cole.
The duo faced each other 14 times in all competitions across club and country, with Ronaldo coming out on top on eight occasions.
Four of their meetings came when Cole played in Arsenal’s colours – with the Hale End graduate winning once – while a further eight came during his time at Chelsea.
With the Blues, he lost five of his encounters, and his luck didn’t fare much better during England’s back-to-back meetings with Portugal in major competitions.
Portugal twice emerged victorious on penalties at Euro 2004 and World Cup 2006.
But from their many clashes together, Ronaldo scored on just three occasions – with two coming in the same match in the Red Devils‘ 4-2 win against the Gunners at Highbury in February 2005.
Ronaldo and Cole first met during the infamous Battle of Old Trafford in September 2003, where in the fifth minute, the forward left the defender with egg on his face.
A rapid-fire skill move completely bamboozled Cole – sending him tumbling to the floor after performing the ‘splits’.
It’s a moment that lives long in the memory of United fans, but despite that, Keown insists Cole proved to be a more than worthy adversary for Ronaldo in the years that followed.
Keown, who played in that 0-0 draw in 2003/04 season, told talkSPORT.com: “I think they were epic battles.
“I think if there was a nemesis for him or his most difficult opponent, it would have to be Ash.
“It was unbelievable the way that Ashley would always… it was almost a double determination from him whenever he played against Ronaldo.”
Keown then stated that went both ways, insisting Ronaldo would be too focused on his battle with Cole, which may have been to the detriment of United.
He remarked: “And it was almost like Ronaldo got fixated with trying to beat him instead of actually switching out and maybe going to the other [side].
“But maybe he felt as if he wouldn’t get anything from [right-back] Lauren either!
“But it was a great battle, something to behold, a game within a game almost.”
Ronaldo himself admitted that Cole was his toughest-ever opponent during an interview with Coach Mag in 2016.
He remarked: “Over the years I had some great battles with Ashley Cole. He does not give you a second to breathe.
“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.”
As for Cole, he opened up on his clashes with his former foe following his induction into the Premier League Hall of Fame in 2024 – insisting he still has nightmares over being humiliated in their first meeting.
The 44-year-old said: “Over the years, Cristiano Ronaldo and I had some mighty battles and we have a mutual respect for each other.
“He came to the Premier League as a little bit of an unknown, but he soon understood what it took to be a top player.
“He was willing to learn and adapt. He wanted to be the best player in the world and became a machine.
“He had everything. He could dribble, he could sprint behind, he could leap and jump and head a ball, he could go inside, he could go outside.
“So I say he always gave me nightmares, but you try to work each other out and we got the best of each other at times.
“Whenever I hear his name or see his face, I always think of when he made me do the splits!”
But for Cole, it’s Ronaldo’s long-time rival Lionel Messi that he named as his toughest opponent – despite the 2018 World Cup winner failing to score against him.
