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Former Top 5 player Brad Gilbert’s best-selling book ‘Winning Ugly’ showed recreational tennis players how to win with strategy and mental warfare in lieu of flashy groundstrokes. It's safe to say Daniil Medvedev fits the mold.

“He has a very weird game. It’s very sloppy, but a good sloppy,” said Stefanos Tsitsipas, who has yet to beat the Russian in their four FedEx ATP Head2Head meetings. “I don’t mean this in a bad way. He’s just very uncomfortable to play against.”

In an era rich with heavy topspin and power hitting from the baseline, the 24-year-old Medvedev offers a throwback with his brand of tennis. He possesses one of the flattest backhands on Tour and uses off-speed shots to frustrate players, imposing his game by taking his opponents out of theirs.

“He has this completely different way of playing, flat and low, without giving you much angle to work with,” said Tsitsipas. “It can be very disturbing to play against him. He can make you miss without understanding why you missed.”

Although his style may not be conventional, it’s clearly working. The Russian reached his first ATP Masters 1000 final last week at the Coupe Rogers (l. to Nadal), finished runner-up the week before at the Citi Open (l. to Kyrgios) and sits at a career-high ATP Ranking of No. 8. On Tuesday, he scored a first-round victory over Kyle Edmund at the Western & Southern Open in Cincinnati.

His winning ways could be why Medvedev is far from insulted by Tsitsipas’ assessment of his “sloppy” game.

“I completely agree,” said Medvedev, cracking a smile. “That’s what I’m trying to do. I want to make people miss with shots that they’re not used to playing. I’ve won many matches because they don’t ever get used to it. I try to find a weak spot in my opponent and then push to it.

“As long as you’re not playing an 18-year-old wild card, you know how everybody plays. If you play Rafael Nadal you know, well, not his weak spots, but what you shouldn’t do… and then you still lose 6-3, 6-0!"

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But while Medvedev prides himself on driving other players crazy, he only recently learned how to stop doing that to himself. The Russian isn’t shy to admit his temperamental past, but credits his recent success with learning how to better control his emotions. Medvedev joked during his runner-up finish two weeks ago in Washington that it was the first time he hadn’t blown up during a tournament.

“I also didn’t get crazy at all [in Montreal],” said Medvedev. “It feels much nicer, but it doesn’t mean that one day, maybe tomorrow, I’m not going to smash three racquets. I’m working on it and hopefully I can continue it for as long as possible.”

Medvedev is also quickly learning that winning brings extra attention. Last year in Cincinnati, he was forced to qualify for the main draw. This year, both of his press conferences so far this week have taken place in the main interview room. But rather than shy away from the attention, Medvedev has embraced it and hopes for more.

“I like interviews as long as you don’t ask me any inappropriate questions,” he joked. "I try not to fake anything. I like to express myself and hopefully show my personality.”

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