Milos Raonic reveals who was the toughest opponent among Nadal, Djokovic, and Federer

Rafael Nadal, Novak Djokovic, and Roger Federer made history as tennis’ iconic ‘Big Three.’ They dominated the sport for nearly two decades, winning countless titles across Grand Slams, Masters 1000 events, and ATP 500 tournaments. With Djokovic now the only active member of the trio, Canadian star Milos Raonic recently shared which of the three he found toughest to face.

Raonic, one of Canada’s most accomplished players with eight career singles titles, often challenged the ‘Big Three’ but never managed a winning record against any of them.

Speaking on The Changeover podcast ahead of the Italian Open, Raonic reflected on his past matchups and singled out Djokovic as the most difficult opponent among the legendary trio.

“The unique thing with Novak was like, even watching other players play him a lot, you get in the rallies, you do all these things right,” Raonic explained. “Novak does this thing where he plays down the middle a lot more than everybody else, but then just takes away angles from you.”

Milos Raonic of Team Canada walk out to the court ahead of his match gainst Daniel Altmaier of Team Germany in the quarterfinal tie between Germany and Canada at Palacio de Deportes Jose Maria Martin Carpena on November 20, 2024 in Malaga, Spain.

Raonic continued: “The strategy wasn’t clear when you played Novak. With Novak, it was like, what do I need to do this time? You’ll lose to him 7-6, 6-4, and you’ll be like, okay I felt good, I was hitting the ball well. Then you’ll watch the match and be like, I felt I was in it—but rewinding it, you’re like, I really didn’t have any chances.”

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Raonic reflects on facing Nadal, Federer, and Djokovic

Having faced all three members of tennis’ iconic ‘Big Three,’ Canadian star named Djokovic as the toughest opponent. He also shared candid thoughts on playing against Nadal and Federer, noting that those matchups were challenging in different ways. “You play Roger, you know what you kinda have to do, it’s a bit more clear,” Raonic said. “But there are a lot of moments where it’s just not up to you. That guy can make you look really, really bad.”

Raonic also explained the unique difficulty of playing Nadal. “With Rafa, the tough thing was that it doesn’t matter how obvious it might be that you have an opportunity to win the match. Before you step on court with him, you know it’s going to take everything out of you because he’s going to be there till the last point.”

Raonic’s record against Nadal, Federer, and Djokovic

Raonic’s head-to-head records offer further insight into his perspective. Against Nadal, he posted a 2–8 record, with his most notable win coming at the ATP Masters 1000 in Indian Wells.

He held a 3–11 record against Federer, including a signature victory in the final of the Brisbane Open, which he won in straight sets. But his toughest battles came against Djokovic. Raonic failed to win any of their 12 encounters, a stat that helps explain why he considers the Serbian his most difficult opponent among the trio.