Who did Lionel Messi & Cristiano Ronaldo name as their toughest ever opponent?
Lionel Messi and Cristiano Ronaldo have spent the last 20 years tearing through defences and rewriting football history.
Between them, they’ve scored over 1,500 goals, won dozens of trophies, and faced just about every top player of their era. But even the greatest have their kryptonite.
From rugged defenders who got under their skin to keepers who denied them time and again, these are the opponents who gave Messi and Ronaldo the most trouble.
Lionel Messi’s toughest opponent
You’d expect names like Sergio Ramos, Giorgio Chiellini or Fabio Cannavaro to show up when Messi’s toughest opponent is mentioned. But when asked in 2020, he gave a different answer.
Pablo Maffeo was just 20 when he faced Messi in 2017, tasked with man-marking him. He stuck to the job like Velcro.
Barcelona won 3-0 that day, but Messi didn’t score, barely had a moment to breathe, and was subbed off early. It wasn’t pretty, but it was effective.
Messi later described the marking as “intense” and named the Girona defender his most difficult opponent. That’s no small compliment from a man who’s beaten the best.
Such praise came as a shock to Maffeo himself. “It was very special that Leo would say that,” he told The Athletic.
“It’s the best recognition from the best player in history. We lost that game, but the experience will always mark my life.”
The pair even chatted mid-match. Maffeo asked about life at Barcelona, and Messi asked about Man City. Then they went back to kicking lumps out of each other.
These days, Maffeo plays for Mallorca, but he’ll always be the answer to one of football’s best trivia questions.
Cristiano Ronaldo’s toughest opponent
Cristiano Ronaldo has gone toe-to-toe with some of the most iconic defenders in modern football, but no one gave him more of a headache than Ashley Cole.
During his first spell at Manchester United, Ronaldo faced Cole 14 times across club and international level.
He only managed three goals in those meetings, with two of them coming in a single Premier League game, and lost eight of the encounters.
Not exactly the kind of numbers Ronaldo usually racks up against full-backs.
“Over the years, I had some great battles with Ashley Cole,” Ronaldo told Coach Mag. “He doesn’t give you a second to breathe… quick, tough in the tackle. You knew it would never be an easy game.”
That relentless intensity was Cole’s calling card. He didn’t rely on crunching tackles or dramatic sliding blocks. He just shut you down, over 90 minutes, across 14 games, and even in your head.
“He always gave me nightmares,” Cole admitted later. “But you try to work each other out, and we got the best of each other at times.”
Cole went further in praising his old rival, saying: “He wanted to be the best player in the world and became a machine. He had everything. Dribbling, pace, aerial ability, movement, he was a nightmare.”
Still, when asked who was tougher, Cole hinted that Messi might have edged it. “On his day, he was just too good for me,” he said. “But again, he never scored.”
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