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WIMBLEDON—Down two sets and trailing 3-0 in the third, Aleksandar Kovacevic challenged a Daniil Medvedev serve, and finally got one right.

He slowly raised a fist and smiled, accompanied by applause from the ever sympathetic Wimbledon crowd.

Medvedev was forced to hit a second serve and proceeded to deliver an ace out wide, chalk flying up in the process.

The spectators sensed the irony and could only laugh this time.

Minutes later, last year’s semifinalist wrapped up a 6-3, 6-4, 6-2 win in a rapid one hour and 46 minutes on No. 1 Court. The “Octopus” faced break points in just one game—saving all three in a row at 5-3 in the first—and won 65 percent of Kovacevic’s second-serve points.

Daniil Medvedev had no trouble with Kovacevic on Monday.

Daniil Medvedev had no trouble with Kovacevic on Monday.

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Truth be told, the New York native’s prospects of upsetting the fifth seed seemed less than ideal. He had never beaten a Top 10 player, he was making his main-draw debut at Wimbledon on a surface he rarely competes on, and he entered SW19 riding a four-match losing streak.

Digging deeper, his last ATP main-draw win came in early April in Houston, having now lost his last six.

But such is Kovacevic’s ability when his game flows that a competitive outing—or even more—seemed a possibility. Coached by John McEnroe in the past, and according to his mom Milanka, being compared to Roger Federer when he was younger, perhaps added to such a viewpoint (well, at least for one author). Indeed, Kovacevic does possess a one-handed backhand and grew into a similar frame as the Swiss.

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If the praise and esteemed tutors suggest Kovacevic spews bravado, nothing could be further from the truth. During a 20-minute conversation with TENNIS.com after his loss, Kovacevic’s mild manner and politeness radiated. Not to mention his honesty.

Achieving the benchmark Top 100 in January, he is nonetheless still coming to terms with the tour’s relentless nature. He may be 25. but Kovacevic delayed his arrival to the pro tour, going to the University of Illinois.

“It’s been tough to be in Europe for a while and not winning much,” said Kovacevic, currently ranked 88th. “We have a little bit of time to spend outside the court, but when you do do one thing and dedicate your life to doing it and it’s not going well, it doesn’t help the rest of your life as well.”

He later elaborated.

“You try to find the things in practice that are positive and things to be excited about for the next week,” he said. “And you are like, ‘Hey, I got it now.’ Then you go and lose first round again and then you are like, ‘Now I got to find things to be positive about again and try to be excited about the next week.’

“It’s been tough to be in Europe for a while and not winning much,” said Kovacevic, currently ranked 88th.

“It’s been tough to be in Europe for a while and not winning much,” said Kovacevic, currently ranked 88th. 

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“And you are also in a new place in Europe and you miss home and you go and lose again.

“It gets to a place where you keep trying and keep failing and keep trying. It’s not easy to go through sometimes. Mentally, it can take a toll a little bit.”

To help, Kovacevic holidayed in France after Roland Garros before going back to the US to practice.

He has found more positives upon his return to Europe—and this time hopes fortunes change. Returning to hard courts after playing on grass in Newport won’t hurt.

“At least I feel like I set myself up for some success in the near future,” he said. “It’s felt like I’ve turned a switch a little bit.”

Brightening his mood was playing on No. 1 Court, “probably the coolest court” he has stepped foot on, quite the admission since he faced idol Novak Djokovic on Court Phillipe Chatrier last year, in his Grand Slam debut.

Milanka and dad Milan watched from the stands Monday.

It gets to a place where you keep trying and keep failing and keep trying. It’s not easy to go through sometimes. Mentally, it can take a toll a little bit. Aleksandar Kovacevic

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Wimbledon’s park-like feel counters the skyscrapers of Manhattan, where Kovacevic grew up, although he did play tennis in Central Park. He began working with Dante Bottini—who formerly guided another player compared to Federer, Grigor Dimitrov—this year. (Dimitrov beat Kovacevic at Roland Garros, one of three Top 10 opponents he has faced in his four Slam main-draw appearances.

Bottini said getting more experience is pivotal for Kovacevic, while also pinpointing other aspects of his charge’s game to address.

“The return side can be one of the areas to improve a lot,” said Bottini, who labeled Kovacevic a hard worker. “The slice and how to play certain points. I think the most is to be a little more organized in his head and, ‘I need to play this type of moment with a bit more decisions,’ or, ‘I cannot give him an easy mistake on this specific point.’ I think that’s the biggest part.

“We’ve been working since February or March, not that long, so I think it takes time for him to understand my philosophy and to start seeing everything on the tour because” of Kovacevic’s limited time in the Top 100 so far.

Kovacevic’s time at Wimbledon concluded Monday in a season providing many a lesson.