Karen Khachanov navigates complicated dynamic to defeat Daniil Medvedev, emerge from shadows in Monte Carlo

Karen Khachanov had seen this movie twice last year, and he hadn’t liked the ending.

In Miami and Vienna in 2023, he had won a set against Daniil Medvedev. His heavy-topspin attack had left his friend and countryman frazzled and agitated. But both times Khachanov had allowed him to wriggle away with a victory. In the end, Medvedev had a few more options, a little more consistency, and a bedrock of confidence that came from having won most of their matches in the past.

On Thursday at the Rolex Monte-Carlo Masters, Khachanov won the first set from Medvedev, and again left him muttering and flashing sarcastic thumbs-up signs toward his coach and wife. But Medvedev didn’t go away, and the Russians fought tooth and nail through a series of long games in the second set.

Khachanov said he tried to move Medvedev “outside the sidelines,” and his tactics put him in control of most of the rallies. He had chances to break, and good looks at second serve, but he couldn’t quite come up with the finishing shot he needed. Was he going to let his friend off the hook one more time? When Medvedev reached set point with Khachanov serving at 4-5, a betting fan surely would have said yes.

But Khachanov felt better about his chances this time for a couple of reasons. First, there was the surface. This was their first meeting on clay, and while Khachanov has never won a big title on dirt, he thinks his playing style works better on it than Medvedev’s does.

“I love to play on clay, with the topspin and the style of play, it suits me a little bit better than him,” Khachanov told Tennis Channel.

Khachanov wasn’t just taking his own word for it, he was also taking Medvedev’s.

“Many times he says he doesn’t like to play on it,” Khachanov said, referring to Medvedev’s well-known, half-ironic insults about clay. “I know it’s a little bit blah-blah-blah, but that gives me a little confidence.”

Khachanov had enough confidence to save that set point at 4-5 with a service winner and go on to hold. That in turn gave him the boost he needed to break Medvedev at 5-5. He also got some timely help from a line judge, who failed to make a call on a forehand that Khachanov hooked wide.

After the point, Medvedev looked at the mark—which electronic replay confirmed was out—and put his hands to head in shock. Two points later, when he had been broken, Medvedev officially flipped. He chucked his racquet into the back wall, and spent the changeover berating tour supervisor Cedric Mourier and chair umpire Carlos Bernardes, who handed him a point penalty for his efforts. Khachanov served out the match without further incident, and completed his first win over Medvedev in six years, 6-3, 7-5.

“Against a friend, mentally, it’s tough to play,” Khachanov said. “Plus his type of game is way different.”

“I think today he lost it a little bit. I have to think, ‘OK, he’s out of his mind; I have to stay focused.’”

I always had good results, basically winning matches, but not going deep to win the tournament...I had some losses against Top 10 guys, but now I’ve got another one. Karen Khachanov

Could this breakthrough lead to more in the coming months for Khachanov? He has been one of the tour’s quietest, below-the-radar forces at big events in recent years. He reached the semifinals at the US Open in 2022 and the Australian Open in 2023, and has been a quarterfinalist at Roland Garros (twice) and Wimbledon (once). It can be tough to recall those results because Khachanov, while he’s a smart, stand-up guy, isn’t a flashy player or a controversial figure.

At 27, ranked No. 17, he thinks the best is still ahead for him. He has already won a title this year, in Doha, and likes his chances even more on clay.

“I always had good results, basically winning matches, but not going deep to win the tournament,” he says of clay-court history.

Success is a step-by-step process, but the last step—beating the elite—has proved to be the toughest for him. Khachanov won the first set against Novak Djokovic at Roland Garros last year, and looked to be the stronger player. But he couldn’t stay steady enough, and couldn’t find a response when Djokovic raised his game.

“To go deeper into the tournaments, and then to think how to beat top guys, and to be at the top. These are the things we have to keep working on,” he says.

“I had some losses against Top 10 guys," admits Khachanov, who lost 23 in a row against the Top 10 between 2019 and 2023 but now, “I’ve got another one.”

Khachanov is also into his first quarterfinal in Monte Carlo. There he’ll face another member of the elite, and another player he has struggled mightily against, Stefanos Tsitsipas. We’ll see if he can change the end of that movie as well, and take the next step upward.