WATCH: Cramping Daniil Medvedev limps over finish line vs. Karen Khachanov in Monte Carlo

A straightforward match turned complicated for Daniil Medvedev, and the former world No. 1 only barely escaped good friend Karen Khachanov, 7-5, 4-6, 6-4—liming over the finish line in two hours and 51 minutes at the Rolex Monte-Carlo Masters.

Looking to avenge a 2024 defeat to Khachanov at this very tournament, Medvedev took big leads in all three sets—leading at one point by a set and 4-1—but Khachanov kept battling back, forcing the match into a decider as night fell over Court Rainier III.

Medvedev, who endured an opening-round defeat at the Miami Open, appeared to have the match wrapped up when won a marathon eighth game to take a 5-3 lead, but Khachanov provided one more twist when he broke the No. 9 seed as he served for the match.

Despite growing physical struggles, Medvedev ultimately eked out the win, but was slow in meeting Khachanov at the net and had perform the camera lens signature from his chair.

Medvedev, who fell out of the Top 10 for the first time in two years at the end of last month, was heard telling the physio that the craps appeared within the final two points of the match, but the 29-year-old was back on his feet for the on-court interview.

“I practiced very well before the tournament, better than I played today, though I played well. It’s the first match on clay, it’s not my favorite surface, so some important points and some shot decisions were not good enough. But I’m happy to win. I watched the matches today on clay and there were a lot of breaks; all of them were up and down. I don’t think Karen hit one ace and he’s a big server. So, it was pretty slow, but I’m happy with my level in general and looking forward.”

Medvedev has famously shown his disdain for clay in the past, but the 2021 US Open champion has shown marked improvements on the surface in recent years: the 2023 Internazionali BNL d’Italia in Rome remains his most recent Masters 1000 victory.

“I was actually unlucky in Doha and Miami because by Miami, I’d been feeling better and better throughout the season. Doha, I was feeling very well during the tournament. But it’s ok; it’s part of tennis. We play 20 tournaments around the world. Everything happens, and we’ve seen it happen with many players. It’s always a little bit tricky, but I feel good. I came back a bit scared after Miami because I was not feeling well there, but did the tests and it was nothing. Just a couple of days rest and I was good to go. So, I’m happy about it.

“I had a long preparation for clay for the first time in probably five or six years, and that helped me to play good today.”

Medvedev will next face Alexandre Müller in the second round.