After two hours and 45 minutes of play on Court 12 Monday afternoon, Denis Kudla hit a serve down the T, forcing an error from Janko Tipsarevic. The Serbian put his hand to his lips, then reached down to the baseline as if to say farewell.

Kudla defeated Tipsarevic 3-6, 6-1, 7-6(5), 6-1 in Tipsarevic’s final Grand Slam singles match. And after four more ATP Tour events (St. Petersburg, Chengdu, Shanghai and Moscow), the Serbian will play Davis Cup and officially retire from professional tennis.

“I was digging today. I spoke to my coach very briefly after the match. This was a sign that it’s time, because I was playing a good first set, not a great second set, but you could see that my energy level, even though I was practising decent for the past 10 days, was going up and down, up and down, up and down. Normally before, when I was playing my best tennis, my energy was constantly up and this was the factor which was overwhelming my opponents, kind of like a David Ferrer way of playing,” Tipsarevic said. “Losing in four [sets] because of fatigue is a sign that I don’t see myself doing this in 2020.”

Retirement has been on Tipsarevic’s mind since the first half of the season. The 35-year-old has undergone seven lower body surgeries, putting his body through the ringer. But he still tried to come back and see how deep he could dig. In Miami, Tipsarevic won his first tour-level match in 570 days.

“As a family we wanted some kind of stability. In the past five years it was quite terrible that we didn’t know what we were doing, because it’s always if you do this, it’s not even what I want or what my family wants, it’s what tennis as a sport needs. So it was always this mix. Am I playing? Am I doing surgeries? Am I recovering? Am I competing? And then surgery again. And obviously all of these ups and downs, no matter how strong I tried to stay, they were really affecting my mood,” Tipsarevic said. “[The first part is] my body. My body’s not allowing me to come to the level where it would make me happy to continue playing tennis. And I’m not even talking Top 10, I’m talking about potentially Top 30. If I don’t see myself that I am able to be Top 30, for me competing and playing tennis is not fun.”

Tipsarevic has also devoted a lot of time to his academy, which he is franchising in four different countries in 2020.

“I’ve been on this guilt trip for quite some time because if I devote too much time to the business side of this because setting all of this up took a lot of time… if I devote a lot of time towards that, I see that part growing and going in the right direction,” Tipsarevic said. “But then I’m not a tennis player. I’m completely something else, and then I put tennis on the third or fourth place in my schedule during the day. And if I devote myself to be a 100 per cent tennis player, this takes six to seven hours.”

The motto Tipsarevic is instilling at his academy and that he has also used during his career is ‘keep digging’. He did not have much left to prove after competing in the Nitto ATP Finals twice, in 2011 and 2012. But even as his body let him down, Tipsarevic battled back.

“When you read fairytales about a hidden treasure, there is normally obstacles. The hidden treasure is somewhere near the end of the book. Normally there is a sea monster and whatever, a hidden map and that’s what you need to overcome to reach it. My big belief is that our hopes and dreams are normally not on the surface,” Tipsarevic said. “If you really want something, you really need to dig. And you really need to dig deep, even when you don’t feel like digging. This is what kept me going and trying to come back. And even if I didn’t, I came back twice. Once Top 50, once 70, but I never regretted it.

“I would regret way more not trying to do it and five years after my first surgery saying, ‘Hey, I earned enough money, I’m going to buy some real estate and enjoy my life.’ But like this, I feel you grow tremendously as a person.”

Tipsarevic has won five tour-level matches this season, but he has not been able to crack the Top 250 of the ATP Rankings. Nevertheless, the former World No. 8 is happy that he pushed himself once again to at least give a comeback a shot.

“I think I really tried everything. A lot of the time in the past few years I had comments, ‘What the hell are you doing, doing all these surgeries and still trying to come back and still working and still practising?’ But I guess this is who I am. This is what made me have a decent tennis career,” Tipsarevic said. “I feel if I didn’t have that aspect of a fighter, I wouldn’t have reached what I have reached in my career. Right now it’s a bit emotional because it’s my last Grand Slam, it’s my favourite Grand Slam. But I’m at peace with it because I feel that it’s time.”

World No. 1 Novak Djokovic has known Tipsarevic since he was nine or 10 years old.

“He was always a role model for all of the young players in Serbia and my generation because he was doing so well,” Djokovic said. “He was the best junior of the world and he was someone that had a very promising career in front of him in professional tennis, judging by his results in junior tennis and had a really good professional career, two Top 10 year-end finishes and also quarter-finals of Slams.”

At the same time, Djokovic knows as well as anyone that his good friend has struggled physically in recent years. It’s less than two years ago that he himself was dealing with an elbow injury.

“It’s sad to see him leave, but at the same time, considering what he has been through with his body in the last three years, it’s kind of understandable. He had a lot of surgeries and injuries. And he just didn’t manage, unfortunately, to get back on that track where he was a Top 10 player,” Djokovic said. “I wish him obviously all the best.”

Tipsarevic owns 286 tour-level wins, four ATP Tour titles and more than $8 million in prize money. But the Serbian does not want to be remembered primarily by his results and on-court accomplishments.

“I want to be remembered as a guy who really gave everything he could, wasn’t able to come back to where he was and still am very happy about it. This sends a message to a lot of young and talented players who are very, very scared of failing because facing reality and giving everything you have, you might face a reality where you see that you’re not good enough. But obviously being Top 10 for two years is something very close and personal to me, something that I wanted all my life I think outside of winning a Slam, which I never did,” Tipsarevic said. “Failed is a big word in that, because everybody’s expecting this fairytale ending that there’s a guy with seven surgeries coming back to his glory days to the Top 10. But it doesn’t really matter. It’s way more important the failing part, because you become a winner in life. If you have this attitude you send this attitude not only to your other businesses, but your friends, families and kids, hopefully, which is eventually how you become a winner.”

Roger Federer has qualified for the Nitto ATP Finals for a record-extending 17th time after winning his first-round match against qualifier Sumit Nagal on Monday night at the US Open. Federer will attempt to capture a seventh season-ending crown alongside five-time former titlist Novak Djokovic and Rafael Nadal, who have already clinched their places, at The O2 in London from 10-17 November.

“I really look forward to returning to London to play at The O2,” said Federer. “It is always one of the main goals to qualify for the year-end event. I love competing there among the other top players.”

Buy Tickets

The 38-year-old Federer competed at the elite eight-player event in 2002-15 and 2017-18, with a 57-15 match record (.792), including titles in 2003-04, 2006-07, 2010-11. He also reached the final on four other occasions, finishing runner-up to David Nalbandian in 2005 and to Djokovic in 2012, 2014-15. 

Federer has compiled 1,224 match wins and 102 titles across his 22 seasons as a pro, trailing only Jimmy Connors’ marks of 1,274 match wins and 109 titles. He has won three ATP Tour titles in 2019, capturing the 100th trophy of his illustrious career with an eighth Dubai Duty Free Tennis Championships (d. Tsitsipas) in March, followed by his fourth Miami Open presented by Itau title (d. Isner) — his 28th ATP Masters 1000 trophy. In June, the Swiss earned a 10th title in Halle (d. Goffin) at the NOVENTI OPEN, which saw him become the oldest tour-level champion since 43-year-old Ken Rosewall at Hong Kong in 1977.

Additionally, Federer reached a 12th career Wimbledon final at the All England Club (l. to Djokovic), where he became the first player to record 100 match wins at a Grand Slam championship with victory over Kei Nishikori in the quarter-finals. He also reached a ninth BNP Paribas Open final in Indian Wells (l. to Thiem).

Federer is currently in third position in the 2019 ATP Race To London, and in the running to become year-end ATP Tour No. 1 for a sixth time (2004-07, ’09), which would equal Pete Sampras’ record of year-end top spot finishes (1993-98). Three-time qualifier Dominic Thiem is next in line to qualify for the season finale in November, followed by Daniil Medvedev, 2018 Next Gen ATP Finals champion Stefanos Tsitsipas, Roberto Bautista Agut and Kei Nishikori, who feature in the top eight. Alexander Zverev, the 2018 Nitto ATP Finals champion, is currently in 10th position.

The ATP’s crown jewel event is to be held at The O2 in London through to 2020, where it has been staged to wide acclaim since 2009. The event has successfully established itself as one of the major annual sporting events worldwide, broadcast in more than 180 territories with global viewership figures reaching an average of 95 million each year.

Roger Federer did not get off to an ideal start to his pursuit of a sixth US Open title Monday evening. But the third seed won, and that’s what counts.

The five-time champion rallied past Nagal 4-6, 6-1, 6-2, 6-4 in two hours and 30 minutes, guaranteeing a record-extending 17th qualification for the Nitto ATP Finals, the season finale at which he has triumphed six times.

“I think trying to forget the first set is never easy I guess in a first round, under the lights. People expect a different result. I expect something else,” Federer said. “I just wanted to pick up my game really, start to play better. I was able to do that. That was a relief, going up 3-Love in the second set, realising that it is on my racquet.”

Federer has now won his first-round match in 62 straight major appearances, improving his US Open record to 86-13 as he begins chasing his first trophy in New York since 2008.

His opponent, Nagal, certainly took advantage of the opportunity in the biggest match of his career to date. The World No. 190 walked onto Arthur Ashe Stadium Monday evening for his first Grand Slam main draw match without having ever earned a tour-level victory. But the 22-year-old showed little fear against Federer, who made 19 unforced errors in losing the first set.

“I wasn’t serving consistently enough. I was hitting double faults that usually I don’t do. Also I was just hitting too many unforced errors. I was in two minds, I guess,” Federer said. “I was able to clear that a little bit. Maybe it’s not a bad thing to go through a match like this. It was very similar at Wimbledon when I dropped the first set there as well in the first round. At the end you look at the last three sets, and they were good. That’s encouraging.”

But Nagal did not prove to have the weaponry to take the racquet out of Federer’s hands. And once the Swiss found his range, he was a train rolling downhill on opening night at the year’s final major.

After staving off three deuces in the first game of the second set, the 38-year-old battled hard to gain an advantage, converting his fourth break point of the next game to take the lead. Federer quickly extended his lead to 5-0, before clinching the 42-minute set when Nagal launched a forehand long.

Federer would break immediately in the next two sets, putting constant pressure on the qualifier, who told ATPTour.com before the match, “I’ve wanted this. I was telling my friends this yesterday. When people told me that Federer plays a qualifier, I was thinking how much I’ve always wanted this.”

Nagal showed his fighting spirit in the fourth set, breaking back for 2-2 with an inside out forehand passing shot that blew past Federer at net. But this year’s Dubai, Miami and Halle champion earned another break in the next game when the Indian missed an inside-out forehand wide, and he never looked back. Federer overcame four break points — including a 0/40 deficit — as he served for the match to move on.

The key proved to be Federer’s pressure. Once he cut down his errors after the first set, he kept on top of Nagal, winning 33/50 net points compared to 7/17 for the qualifier.

“He loves putting pressure on the other guy,” Nagal said. “He’s always making you think of what he’s going to do, and that’s how I felt. Players I have played, I never had this feeling. But what he was doing so good was he was mixing it so well that you have no idea where the ball is coming back. So you always have to react to it.”

Federer had lost a set in his first-round match at the US Open just once since 2003 (2017 vs. Tiafoe). The 20-time Grand Slam champion has not fallen in the opening round at a Grand Slam since 2003 Roland Garros. 

Damir Dzumhur, who beat French qualifier Elliot Benchetrit 4-6, 6-2, 6-3, 6-0, awaits in the next round. Federer will take confidence knowing he defeated the three-time ATP Tour champion in straight sets at Roland Garros and Wimbledon in 2015.

Another Swiss was challenged Monday evening on nearby Louis Armstrong Stadium, as 2016 champion Stan Wawrinka needed two hours and 49 minutes to beat #NextGenATP Italian Jannik Sinner 6-3, 7-6(4), 4-6, 6-3.

Sinner, who rallied from the brink of defeat in the second round of qualifying, showed the level that has helped him climb from outside the Top 1,000 53 weeks ago. But Wawrinka’s experience paid off in the big moments, converting five of his 10 break chances compared to Sinner’s 4-for-14 rate. The former World No. 3 struck 35 winners to advance to the second round for his ninth consecutive appearance in Flushing Meadows.

Wawrinka avoided going five sets, saving two break points as he served out the match. The 34-year-old will next face Frenchman Jeremy Chardy, who battled past Winston-Salem Open champion Hubert Hurkacz 3-6, 6-3, 6-7(6), 6-1, 6-4 after three hours and 13 minutes. Wawrinka has won all five of his FedEx ATP Head2Head meetings against Chardy. 

Lucky loser Kamil Majchrzak, who took Milos Raonic’s place in the draw, outlasted Chilean Nicolas Jarry 6-7(2), 7-6(5), 7-6(6), 1-6, 6-4 in three hours and 40 minutes. The Pole will next play Uruguayan Pablo Cuevas, who defeated American wild card Jack Sock 6-4, 7-5, 7-6(5).

Lithuanian Ricardas Berankis, who leads the ATP Challenger Tour with four titles this year, ousted Czech Jiri Vesely 4-6, 7-6(4), 3-6, 7-6(4), 6-4 after four hours and 16 minutes. Berankis will try to reach the third round of the US Open against Spaniard Pablo Carreno Busta, who upset No. 19 seed Guido Pella 6-3, 4-6, 7-6(2), 6-3 in three hours and 13 minutes. 

After the US Open singles draw came out on Thursday afternoon, Denis Shapovalov texted fellow #NextGenATP Canadian Felix Auger-Aliassime to let his good friend know that for the second year in a row, they’d be facing one another in their Flushing Meadows opener.

“That’s how he found out, actually. I just made a joke. He was like, ‘Are you serious?’ I’m like, ‘Yeah, man!’” Shapovalov said. “I’m like, ‘Yeah, I think we’re going to be playing each other for the rest of our lives here.’ Regardless if we’re both seeded [in the future], it doesn’t matter. They’re going to put us first round.”

A year ago, Shapovalov was in the stronger position of the two, seeded 28th, whereas Felix was ranked outside of the world’s Top 100. The 2016 US Open boys’ singles champion, Auger-Aliassime was pursuing a breakthrough. And it appeared he might have gotten his shining moment under the lights in New York, where he took the second set from Shapovalov.

But instead of a tremendous victory, heartbreak followed. A reoccurring heart condition forced Auger-Aliassime to retire in the third set. And instead of both #NextGenATP stars walking off the court full of pride, they emotionally embraced on Shapovalov’s side of the court.

“It was a very difficult moment I think for both of us, obviously more for him. [It was his] first time qualifying for a Grand Slam, playing a fellow Canadian that he grew up against and going out like that, it was pretty tough. It was pretty emotional,” Shapovalov said. “Obviously right after the match I went to see how he was doing and I talked to the team and they said he’s a lot better, his heart is just going down, his heart rate.”

That wasn’t the last the friends — or for the day, opponents — would see of each other that day, though. It’s not often that opponents spend quality time with each other later in the day after they compete against one another, but that was the case last year.

“A couple hours later I was getting treatment at the hotel, we were staying at the same place, so I just said come on over and we just started laughing about it. [We were] just talking, the tennis part of it was gone and we were just able to be friends in that moment,” Shapovalov said. “I thought it was actually an amazing moment because you go from something so traumatic and so scary to a couple hours later we were joking about it like it’s nothing and we were back to being good buds.”

This time, they will hope to let their tennis define the moment. Auger-Aliassime has rapidly risen the ATP Rankings this year, earning the 18th seed here in New York, setting up for a tantalising first-round encounter, even if they’d prefer not to play one another immediately.

World No. 33 Shapovalov made sure to note that this is not a unique situation, though. Stan Wawrinka and Grigor Dimitrov have played in the first round of four tournaments since Wimbledon last year.

“Honestly it is what it is. It happens a lot,” Shapovalov said. “It’s unfortunate to play a guy from the same country so early in the tournament, but I honestly just treated it as any other match. I think I’m playing well and I’m really looking forward to it. I think I’m coming in here in good shape and regardless of who I play I knew it was going to be tough. Honestly the draw could be tougher. I could be playing Roger or Novak in the first round. So I’m looking at it in a positive way as well. It’s definitely going to be a tough one, but a really exciting match.”

One difference this year is that Shapovalov has a new voice on his side. The lefty began a trial at last week’s Winston-Salem Open with former World No. 8 Mikhail Youzhny.

“I think so far he’s helped me a lot,” Shapovalov said. “Tennis-wise, too, but I think mentally speaking, I’ve talked a lot with him and just having that player opinion. He’s gone through so much in his career, it’s perfect to have him alongside with me.”

Auger-Aliassime once showed Shapovalov a screenshot of when the latter won one of their junior matches 6-0, 6-0. But Tuesday’s popcorn match of the day figures to be a thrilling affair, between two friends and tough competitors.

“It’s definitely a tough matchup. In terms of tennis-wise, he’s been playing unbelievable all year, all season, so it’s definitely a tough one. But I managed to pick it up the past couple weeks, especially in Winston-Salem,” said Shapovalov, who made the semi-finals at that ATP 250 tournament. “I think it was the perfect call to go get a couple matches in. I feel pretty confident, pretty ready and it’s going to be a great match.”