As Novak Djokovic recently discovered, sometimes the ball simply doesn't bounce your way.
Despite his No. 5 in the world ranking, the Serbian tennis player couldn't serve up a victory in the opening round of the US Open's men's singles draw, losing to Argentina's Mariano Navone, 25, Aug. 30.
"I didn't enjoy myself," the 24-time Grand Slam winner acknowledged to reporters, referencing the slew of ailments he enduring during the four-and-a-half-hour match.
"It's something that I've been carrying, unfortunately, pretty much every match this year: Vomiting, throwing up, a serious issue there," he explained. "Then my whole body starts to collapse, basically cramping and pain. Yeah, the back just gave up in the end, and shoulder, and I couldn’t close it out."
Basically, there hasn't been a lot of love in the sport for Novak as of late.
"I've been dealing with it for many years now," he told reporters when forced to request a medical timeout ahead of his defeat at the Cincinnati Open Aug. 15. "It causes me a lot of problems, especially when there’s a lot of humidity and heat."
So, no, work hasn't been going so hot for the dad of two.
And, yet, despite his earliest exit in a Grand Slam since the 2006 Australian Open, one could argue the 39-year-old stays winning.
Having banked nearly $200 million in career prize money and netted partnerships with Hublot, Lacoste and Qatar Airways, the athlete—named a global strategic advisor for investment firm General Atlantic in June—is able to hold court in New York City, Monaco, Spain and Greece.
And until 2025, home court for he and wife Jelena Djokovic—they wed in Montenegro three months before welcoming son Stefan in October 2014—was a three-bedroom penthouse overlooking Lake Pavlova in their native Belgrade.
The pair had founded his eponymous foundation there, focused on early childhood education (Jelena serves as the global CEO), and built the 14-court Novak Tennis Center, while his parents Srdjan and Dijana served up the Novak 1 Cafe & Restaurant.
But in November, Novak confirmed the chatter that they'd decamped to Athens amid ongoing tensions between him and the Serbian government.
"It wasn't something I had planned for a long time," he explained to Greek outlet SDNA. "Actually, in the last two years, things have happened, decisions have changed in our lives, both privately and professionally. But that’s okay, that's how life is."
Having enrolled their kids (daughter Tara joined their team in September 2017) in nearby schools, "we are trying to adapt and find the best environment for them as well," Novak added. "Because that is the priority, how the children will grow up in the most beneficial environment for them for their psychological, physical, and emotional health. To be in an environment where we feel like we have more time as a family, privately."
And should Athens ultimately not feel like a winner, they could bounce around to their seaside enclave in Monte Carlo, the nine-bedroom mansion in Marbella, Spain, where they spent most of the pandemic or one of the two 2,000-square-foot units they own in NYC's SoHo neighborhood. (He sold his oceanfront Miami penthouse for $6 million in 2021.)
Of course, more often than not, Novak finds himself bunking somewhere else entirely.
When on the tennis circuit, "missing out on some important dates and events in their life…it’s hard," he admitted on CBS Mornings in July of budding tennis player Stefan and Tara, who's more interested in ballet and gymnastics than the family business. "That’s why I don’t play as much as I used to, because I want to be the best husband, father, brother, son that I could possibly be."
It's what's driven him since he picked up a racket at age 4, despite coming from a family of professional skiers. Asked the quote he lived by, Novak told ATPTour.com last November, "One of my favorites is, 'There is no elevator to success, you have to take the stairs.'"
And he and Jelena, 40, have shared quite the climb.
Despite meeting in high school in the late '90s, they reconnected in 2005 while she was studying in Milan, spending much of their early years on opposite ends of the proverbial court.
"I was a student barely getting by, and he was a very young tennis player who also had no money to spare on expensive trips," she has explained. "Airplanes were, at the time, something utterly out of our reach. We contrived and devised these plans how to meet, how to make our relationship work."
Among their strategies is knowing when to volley any issues around, Novak recently noting to People, "the more you keep it inside, the more the monster grows."
By the time he wed the business grad at a five-star resort overlooking the Adriatic Sea, he was days removed from winning his second Wimbledon title and building his reported $30 million fortune, something he knows wouldn't have been possible without his forever pairs partner.
"She's the only serious relationship I ever had," he told People. "She's been my girlfriend, fiancée and my wife for more than 20 years, and I'm eternally grateful for her love, her support, the relationship that has evolved over the years."
And he's not the only tennis start to net a strong romance. We're serving up the details on how other athletes scored their winning relationships.
Few people are strong enough to volley back and forth with the tennis great. But Reddit cofounder Alexis Ohanian showed off some real skills during their first 2015 date. With Williams' assistant and agent tagging along, "They just bombarded me with questions—it was like two hours of interrogation," he recounted in an episode of her 2024 ESPN+ docuseries In The Arena. "'Do I have kids? Am I married?' Nothing was off limits."
Soon after, the answer to both was a firm yes, the pair welcoming daughter Olympia in 2017 before marrying later that year. (Daughter Adira rounded out the team in 2023.)
"Having someone as special as Serena as a partner is a consistent reminder of self-improvement," the tech entrepreneur explained to E! News in 2023. "I knew I have found someone I was going to spend the rest of my life with because she was someone who I knew I would never outgrow."
The seven-time Grand Slam winner nearly faulted on her forever with Italian actor-producer Andrea Preti. In Lake Como with her sisters, she received a last-minute invite to the Gucci show at the 2024 Milan Fashion Week, she recounted to Vogue ahead of their December 2025 vows, "and decided to go on a whim, and Andrea was tired. Neither of us was planning on being there."
But he aced his pick-up line and soon after they found themselves roaming the streets of London. Following those initial dates, detailed Venus, "I just knew I was going to marry him. People always say they just know, and I just knew."
Even as the top player in the world, the Italian athlete knew he could ace a strong relationship. "Of course it's not easy, I travel a lot and during tournaments I'm very focused," he noted to Vanity Fair Italia in 2024. "But I think it's a wonderful thing when you find the right love. If you think about it, the best tennis players in the world all have wives and children."
And he seems to have met his match in Danish model Laila Hasanovic. Hard launching their romance in his 2025 Vienna Open victory speech, Sinner shared, "To understand me at times, it is not easy, but thank you for putting in the effort. Everyone here, with family, my girlfriend, friends."
Well before the No. 4-ranked athlete wed fellow New York native Taylor Gahagen in 2021, they were in the same circuit. After Gahagen earned his MBA, he took a job working for her parents, who happen to own the Buffalo Bills.
And though he no longer holds court at Pegula Sports and Entertainment, he's still playing proverbial doubles with Pegula, serving as vice president of her skincare brand Ready 24 and helping run their charity, A Lending Paw. "We wanted to help people afford service dogs," Pegula told Vogue of their mission. "Not only is it about dogs helping people, it’s about people helping dogs, because we only work with rescues. It goes both ways."
Even after the WTA's current top player won the Brisbane International tennis tournament in January 2026, she continued to serve. "Thank you to my boyfriend," the Belarusian athlete shared, adding pointedly to Georgios Frangulis, "hopefully soon I can call you something else."
Fortunately, the Brazilian businessman didn't drop the ball. Two months later, he popped the question to his partner of two years with a stunning 12-carat custom diamond. "It was super cute," the Oakberry founder acknowledged in a June 2026 episode of the Open Residency podcast, "but I was already planning to propose long before that."
A new sporting power couple emerged when the tennis player and soccer star Trinity Rodman sealed their relationship with a kiss on Instagram in March 2025.
And she's been a stalwart supporter throughout the Grand Slam tournaments, including slamming reporters who invoked her estranged dad Dennis Rodman.
“For Ben’s matches he has his family there as his support system, which includes his dad,” Rodman wrote on a July 2025 Instagram story, calling out the Wimbledon broadcasters for their commentary about her family. “My dads not even in MY life no need to bring him up during HIS matches when I don’t even want him talked about during mine.”
After the pair met on Raya, Fritz made his relationship with Morgan Riddle official in 2020 with the influencer continue to root him on as he worked his wayup the ATP rankings.
“I met him and started travelling with him on the tour a few months later,” she told E! News in 2024. “And now, it’s been almost four years of that.”
However, in April 2026, Riddle confirmed that she and Fritz—who was married to fellow tennis player Raquel Pedraza from 2016 to 2019 and welcomed son Jordan in 2017—had broken up after six years together.
For years, the two-time Grand Slam champ lobbed away any stories of her personal life.
“I think I felt like I just, some parts of myself I love to share and then some parts I think I just keep to myself,” she told People in March 2023. “So I do feel like my life is a little bit in my hands too.”
Still, boyfriend Jalen Sera—an Atlanta-based musician whose fourth-grade teacher was coincidentally Gauff’s mom—has proven to be an important sounding board.
"Last night, I started a little bit, but honestly, I just called my boyfriend," Gauff told reporters about her 2023 US Open Win. "And I told him let’s talk until it's time to go to sleep so we spoke until 1:00 am and then I went to sleep."
Dimitrov and Eiza González made their relationship Instagram official in May 2025, just one month after sparking romance rumors. And since then, the Baby Driver star hasn’t held back in showing her support for the athlete—including after he had to withdraw from the Wimbledon in early July 2025 due to a mid-match injury.
“Love of my life. I couldn’t be more proud of you,” González wrote on her Instagram Story at the time. "This is just a moment that will pass and will make you even stronger. But watching you today alongside the world was a reminder of who YOU are. You’re a winner. We all saw it. And you’ll do it again. I love you."
After almost five years of dating, the tennis stars announced their engagement in 2024, with Boulter captioning the happy moment, “We’ve been keeping a small secret.”
The pair met in 2020 at a hotel where they were both staying. "We bumped into each other at six in the morning and ended up getting a coffee," Boulter recalled to the Sydney Morning Herald in June 2024. "From that moment, I knew I was in it for the long haul."
They sealed their partnership with fairytale Tuscan vows in July 2026.
In January 2025, the four-time Grand Slam champion confirmed her breakup with rapper Cordae after five years together. And while emphasizing that they remain friends, she expressed gratitude over their romance as it brought them their 2023 arrival little girl Shai.
"Honestly really glad that our paths crossed because my daughter is my biggest blessing," Osaka wrote at the time. "And I was able to grow a lot from our experiences together."
Paul may have the skills on the court, but his bride Paige Lorenze is a go-to coach when it comes to life outside the sport.
"She's been on me about, I guess it’s self-care," Paul told People in April 2025 of the woman he partnered up with in 2022."But just putting on more sunscreen and doing moisturizer at night."
Still, the Dairy Boy founder is no stranger to picking up a racket. "I'm not going to lie, I’m pretty impressed," Paul gushed about her tennis game. "She plays pretty good, she has the strokes down. She knows what she’s doing on the court."
She stuns off the grass as well, overseeing all the details of her and Paul's July 2026 vows in New York.
"Having everyone we love together in one place was incredibly special," she shared with Vogue. "And in many ways, celebrating with them felt just as meaningful as celebrating each other."
The tennis stars are in sync on and off the court. In fact, they met after Svitolina won the 2018 WTA Finals in Singapore, going on to tie the knot in July 2021. A little over a year later, they welcomed their baby girl Skaï.
"I had the most amazing night of my life, which ended with the most beautiful girl around 6:00 am. Elina was strong and brave," Monfils wrote on Instagram in October 2022. "I can't thx enough, my wife, and God, for this special moment. Welcome to the world, my little princess Skaï."