Game, Set, Perfect Match: The History of Anna Kournikova and Enrique Iglesias’ Super-Private Romance

You can run, you can hide, but ultimately there’s no escaping Enrique Iglesias and Anna Kournikova‘s love.

The Grammy-winning singer and the tennis champ first met in late 2001, when Kournikova took the role playing Iglesias’ love interest in his “Escape” music video, a TRL hit for the new millennium—and, while there were some things to sort out before they could be together forever…

It was game, set, love match.

“She’s beautiful, talented, great tennis player,” Iglesias said appreciatively but nonchalantly about his co-star in a Making of the Video feature. “…It doesn’t take a good actor to kiss Anna and try to make it believable.”

After spending the better part of two decades as one of the most private of high-profile couples, having successfully surrounded themselves with tight-lipped people who obviously have better things to do than leak details about the couple to inquiring minds, they confirmed last week via Instagram—their version of shouting news from the rooftop—that their third child together was born on Jan. 30. They’re also parents of 2-year-old twins Nicholas and Lucy.

Though she did share a teaser for Iglesias’ “Subeme la radio” video in February 2017, Kournikova’s Instagram page pre-babies mainly revealed that she was deeply committed to working out and in a serious relationship with her beloved dogs. Same for Iglesias, whose pre-fatherhood account was devoted to touring, music, fans—and the dogs.

He basically gave a preview of what would be his Instagram account one day when he told The Guardian all the way back in 2010 that he was the happiest “at home with my dogs, or on the boat going waterskiing on a beautiful day in Miami. And having a hit song that connects with people.”

He and Anna respectively wished their canine son Jack a happy birthday on Oct. 9, 2017, about two months before their human babies were born without the couple having let on that they were expecting. To this day, they remain as low-key about their enduring partnership as ever—and the dogs still factor prominently in their public photo albums.

But about the things that needed sorting out before they settled down…

When Anna and Enrique first met, she was barely 21 and had been linked to two much-older Russian hockey players, Pavel Bure and Sergei Federov, off and on since she was about 16.

She and Federov, who won three Stanley Cups with the Detroit Red Wings, are said to have first met in Moscow when she was 15. Kournikova moved to Florida for tennis and, as she improved as a player and her model looks made her an instant endorsement darling and lad-mag pinup, Federov was regularly in the picture.

Though she denied a July 2001 rumor that they secretly got married in Russia (ring watch is timeless, people), Federov claimed to The Hockey News in 2003 that they had been married, “albeit briefly, and we are now divorced” (as well as no longer in touch). She was also rumored to have been engaged to Bure—who knew Federov from the Russian national team (dating back to when it was still the Soviet national team)—as late as 2000. She and Bure both denied being engaged.

What a web.

“While I don’t typically comment on my personal life, let me confirm once again that I am not married,” Kournikova stated on her website. Her father similarly told reporters he knew nothing about an alleged wedding.

According to the Telegraph in 2003, she later responded to a request for comment with, “Why don’t you go and find out? I really don’t want to talk about it.”

Federov said yet again in 2005, talking to ESPN.com, that he and Kournikova were briefly married—and that their relationship was, for one thing, misunderstood, and that it had its highs and lows.

“The best thing was that we were both Russian. There was no romance for a long time. She was just a kid when we met the first time,” Federov, who’s 11 years older than Kournikova, said. “Our families got along. We had a lot in common, we lived similar lives, we understood each other. So our friendship developed ’cause we were in the same position professionally and socially.”

The progression to romance came as a surprise to him, he recalled.

“We spent quite a few days together,” the athlete told ESPN. “Anna expressed that kind of interest, I was kind of surprised because I was a little bit older and wilder than her and I was going in a different direction. But I looked at the situation and said she was a great person, so why not? So, then we started dating. It was tough because her schedule had her based all over the world and I played games in so many different cities.” Their marriage, Federov continued, was the “same as the normal life we led before. We were both glued to our schedules. It was just a normal thing couples do when they reach a certain stage of their relationship.”

His buddies never let him forget it. When Federov was inducted into the Hockey Hall of Fame in 2015, his former coach Scotty Bowman reminisced about letting the player leave the team to go work on his relationship, Yahoo! Sports reported.

“They were pretty serious. He wanted a couple of days, and we were going to Los Angeles,” Bowman recalled. “I said, ‘Why don’t you go there first and then rejoin the team. He could miss a practice.”

“I had trouble off-ice. With my love life and stuff,” Fedorov said. “One moment I really cherish is when he let me off the team for three days.” He said he “played even harder” for his coach after that show of support.

So no wonder Kournikova and Iglesias, the son of an internationally renowned entertainer who’s familiar with how nutty the tabloids can get, do not splash their romance all over social media. And, true to form, the most solid hint yet that they did go out and get married at some point is the fact that Anna is “Anna Kournikova Iglesias” on Instagram.

“I think it comes with the territory,” Iglesias told E! News in March 2014. “I understand why people ask, ‘Are you married? Do you have a girlfriend? Do you have kids? Do you have kids that we don’t know about?'”

He explained, “When I go back home, I want to make sure that whatever goes on in my house, it’s just for me and my loved ones that are with me right there. I need that.”

Whether she and Federov ever tried marriage on for size or not, Kournikova and Iglesias had met by the end of 2001. The sexy “Escape” video premiered in January 2002 (“we’re trying to get as much sex in this video as possible,” Iglesias quipped) and they attended the MTV Video Music Awards together that August. The stars had simply aligned for the Spanish singer and Russian tennis player, both of whom had adopted Miami as their hometown; loved sports, the sun and being on the water; and understood what it was like to be on the road for weeks or months at a time.

And they’ve been gleefully leading people on a like-minded goose chase, ranging from low-speed to wild, ever since.

Plagued by injuries, Kournikova actually retired from competitive tennis in 2003 (she never won a singles championship but had 16 in doubles, including two Grand Slam titles), though she’d continue to play in exhibitions and other related events for years to come, and she remained one of the most talked-about and, at times, controversial athletes in sports.

“I know what it’s like to be judged, dissected, picked apart for all of my life,” Kournikova told the Los Angeles Times in 2011, when she joined The Biggest Loser as a trainer. “It was so painful. I was just a kid at the time. I was being judged over here for being too pretty, or over there for not looking good enough. And God forbid I gained a pound. I heard about it. And then I was being criticized for not being a good enough tennis player and yet I knew—I knew—I was giving it everything I had.”

In 2004 she and Iglesias sparked secret-marriage rumors (denied) and in April 2007 he told People en Español that he wasn’t sure if he foresaw marriage, or even happily ever after, for them. “The only thing I can say is that, in my opinion, Anna, whether we are together or not, would be an ideal mother,” he said.

The following month he further mystified people, reportedly telling Sweden’s Aftonbladet that not only did they break up…

“We’re divorced. I am single now, but that’s okay,” he was quoted as saying. “I don’t mind being alone.”

After the déjà vu had worn off, Anna’s rep said the singer had been joking and they were still together after five years of dating.

Meanwhile, she did have her own thoughts on the subject, which she eventually became comfortable sharing.

“I’m never getting married,” Kournikova told People in 2008, but added that “everything is good” on the personal front.

She explained her own approach to trying to maintain her privacy amid all the public interest to The Guardian in 2008, saying, “Girls look at him. Guys look at me. It goes with the job, but it gets annoying when you feel violated. Just take the picture and be done.'” You could almost hear the shrug.

“I’m not married, not pregnant, didn’t have a boob job, no Botox. What else?” Anna offered.

That being said, Kournikova wasn’t accompanying herself on a tiny violin or anything.

“Hey, I took the money,” she said, referring to the perks that came with her tacit agreement to be in the public eye. “It’s simple. If you don’t want the attention, don’t take the money.”

Kournikova reiterated on The Graham Norton Show in 2010 that she and Iglesias had no plans for marriage. “We’re fine—we’re perfect…Being eight years together, it’s more [time] being married [than most] Hollywood couples, or whatever.” (“Common law now,” agreed fellow guest Katy Perry.) 

But in 2011, Anna told Women’s Health that she did want to have children, “whether I have my own or adopt. I love taking care of people.” 

“[Marriage] isn’t important to me,” she continued. “I’m in a happy relationship—that’s all that matters. I believe in commitment. I believe in being open and trusting each other and respecting each other completely.”

Finding a like-minded partner is also key.

“I want my personal life to be as private as possible,” Iglesias said in an interview with Australia’s Today Tonight in 2011. “And especially when you’re with someone that’s also known and in the spotlight.”

“It’s not that tough [to stay under the radar],” he added. “You’ve got to have a sense of humor. I’ve been married about 28 times, have kids all over the world. In Australia…I think I’ve got twins in Australia, in Perth. Truly, you just laugh at it.” (In 2014, he trotted out the divorce joke again—he must be great at dad humor already—when he told reporters in Los Angeles, “I got a divorce three days ago and I wanted to give you guys the exclusive. I’m serious. No, seriously. Don’t laugh.”)

Meanwhile, marriage apparently hadn’t been on the table yet, despite the impressive diamond rings Kournikova enjoyed sporting over the years. 

“I’ve never really thought marriage would make a difference,” Iglesias told Parade in 2012. “Maybe it’s because I come from divorced parents, but I don’t think you love somebody more because of a piece of paper.”

The youngest of three born to Spanish super-star Julio Iglesias and his first wife, Maria Isabel Preysler-Arrastía, Enrique has a notoriously prickly relationship with his father, who went on to have five more children with his second wife. Enrique told The Guardian in 2010 that the person he most admired in life was “Elvira, the lady that took care of me when my parents weren’t able to be there. She dedicated her whole life to me and my brother and my sister. Now I take care of her.”

In 2014, Julio Iglesias told The Mirror that he had never met Kournikova, though he wholeheartedly approved of the match.

“My kids are very independent and it is difficult to see Enrique because he is all over the world,” the singer said. “But Anna is very beautiful—they have good taste, my kids.”

Enrique’s mother, siblings, stepmom and step-siblings had met Anna, though, Julio said, and he was confident that his son was doing well. Meanwhile, Enrique’s mom, sister and brother all expressed their excitement when the twins were born in December.

“It was a perfectly normal pregnancy, she didn’t have to do mandatory bed rest at any time,” the babies’ grandma Isabel Preysler told Hola! “Anna hasn’t had to hide. She has a very simple and homey life.” 

Iglesias wasn’t a regular in the crowd while Kournikova was still playing, presumably not wanting to be a distraction, but they do like to watch tennis together. They were photographed in the stands at the Los Angeles Tennis Center in 2004, and then popped up at what’s now the Miami Open, held annually in Key Biscayne, to watch Serena Williams play in 2009. Asked in 2007 if he could beat his girlfriend at any sport, Enrique confidently told Sports Illustrated, “Anything except tennis and wrestling. Her reflexes are disturbingly good. You throw anything at her, and she catches it.”

Dating an athlete, Iglesias said, has made him respect athletes 1,000-times more. “In music you can start whenever, 18 or 19 years old,” he told SI. “If you want to be an athlete, you have to start when you are 4 or 5. There is so much dedication, so many hours, mentally and physically. Sometimes your mind wants it so much but your body cannot handle it.

“Anna took to me the place where she was brought up in Russia and if you see the house she lived in, you can open up your arms and touch it wall to wall. Out of there, she played every single day for eight hours since she was 5 years old. For me, it’s mind-boggling. To me, she is the most amazing person I have ever met.”

They’ve been all over the world on vacation like glamorous celebrities, but part of their charm is that they usually keep date night local like regular people, whether they’re catching a Miami Heat game or just going out to dinner, or taking their boat for a spin (that’s considered regular in Miami Beach).

In fact, after they were rumored to have broken up in 2013, the inevitable rumor-quashing pictures of them on the boat were forthcoming.

Kournikova also said on The Graham Norton Show that they had their ordinary-couple issues just like anybody else. Asked if Iglesias left his wet towels lying around, she said, “Yeah, and you find underwear, you know, everywhere and dirty socks and everything.” 

“At least it’s Enrique Iglesias’ dirty underwear,” Norton quipped. “Put it on eBay.” “I probably could!” Anna agreed.

But that’s as much dirty laundry as we should expect to hear about firsthand.

“I keep my personal life as private as possible because I feel that we need that,” Iglesias said on CBS Sunday Morning in April 2014.

Asked about his past comments regarding marriage, he clarified, “I didn’t say that I don’t want to get married. I don’t know if I maybe came out the wrong way. What I said is that, ‘We are extremely happy the way we are.’ I’m not against marriage by any means.”

He continued, “I have not ruled it out, but if you’re happy, I don’t think it will really make a difference. She’s the coolest girl in the world.”

Meanwhile, Kournikova embodied the perfect-day scenario he had been describing for nearly a decade.

“A day off for me is being at home on the sofa, watching TV with my girlfriend and our two pets—just having a good time,” Iglesias told Ventaneando in October 2017.

Even more telling, he added, “I would love to have children. Hopefully very soon. I think I’d be a good father, my girlfriend would be an even better mother, but I’d be a good father.”

The couple had two months to go before their carefully laid plan came to fruition.

“It’s incredible to watch her be such a great mother,” Iglesias told The Sun in October 2018. “It’s incredible to watch a mom do what she does, when a mother’s instinct kicks in.” And, asked whether becoming parents had put a damper on their alone time, the singer informed the tabloid that “the sex has not diminished.”

 Apparently not.

(Originally published June 7, 2018, at 3 a.m. PT)