Tennis is a sport loved by many people worldwide. We are now in the Open Era, the era of professional tennis. It began back in 1968 when the Grand Slam tournaments allowed professional and amateur players to compete with each other. That ended the strictly professional era that started in the 19th century.
Tennis players are at the center of our interest. Most of them, because of their accomplishments – we love to cheer them on and bite our nails when they are competing. But some people want to know more about them. That includes their romantic lives, tabloid stories, and interesting facts.
We’ll focus on famous tennis playboys from this century. You’ll learn all you want and need to know about them.
The Difference between the 20th and 21st Century
Do you remember how things were back in the 80s and the 90s? The Internet just started its journey. Children played outside, and cell phones were something from an SF movie. But, all tennis enthusiasts and lovers remember that period as a dominant era of Boris Becker. He was successful from the beginning of his career, winning the Wimbledon Championship when he was only 17. He had trouble dealing with his early fame and success. Furthermore, he filled tabloids with his relationships with Karen Schultz and Cassandra Hepburn before he married Barbara Feltus in 1993.
He was considered a tennis playboy of the 20th century, and that was without online dating sites. We can’t imagine the headlines if a one night friend hookup was available back then.
Nowadays, finding a one-night stand has never been easier. There are dating sites specialized for that type of relationship, such as Onenightfriend. They’re growing daily. When creating a profile on a dating site, users want to be sure that they’ll find a person that fits their preferences. A Hot or Not game ensures just that. By swiping left or right, users are giving valuable information to algorithms. Based on the profiles they liked, the algorithm matches them according to their preferences. Another feature users can benefit from is video chat. Some people love to text, but others love seeing their potential partners. With this feature, things can spice up and go to the next level.
Read on and learn about the most famous tennis playboys of our era.
1. Mark Philippoussis
Mark Philippoussis (1976) is a former Australian tennis player. He started playing tennis when he was only 6 years old. In 1994 (at 18 years old), Mark became a professional. In 1996, he got to the 4th round of the Australian Open, upsetting Pete Sampras. When he was at the peak of his career, he was known as having one of the fastest serves. In 1999, Philippoussis entered the top 10 for the first time and stayed there for 10 weeks.
His father is Greek, and his mother is Italian. That combination is perfect for driving ladies insane. He had a minor career as a model and even starred in the reality dating show Age of Love. He filled the tabloids when he allegedly dated Paris Hilton while with Delta Goodrem. That ruined his public image and was the beginning of his fall. In 2005 he was engaged to Alexis Barbara but ended it before filming Age of love. He’s now married to Silvana Lovin (since 2013), with whom he has two children.
2. Andy Roddick
Roddick is an American former world’s number one tennis player. Andy won the 2003 US Open and reached four big finals (Wimbledon in 2004, 2005, and 2009, and the US Open in 2006). Each time he lost to Roger Federer. For 9 consecutive years, he was in the top 10 players in the world.
Roddick is the most recent North American man to win a singles major (2003 US Open), the last to hold the world No. 1 ranking, and the most recent to claim the year-end world No. 1 ranking. He retired from professional tennis in 2012 and got introduced to the International Tennis Hall of Fame in 2017.
There were rumors about Andy dating Ashley Harkleroad, Paris Hilton, and Maria Sharapova. He dated Mandy Moore from 2002 to 2004. He met his now wife (Brookly Decker) in 2007, got engaged in 2008, and by 2009 they were married. They are still together and have one son.
3. Grigor Dimitrov
This professional Bulgarian tennis player is the highest-ranked Bulgarian player in their history. He went pro in 2008, but before that, he thrived in his junior career. In 2013 at the Stockholm Open, he became the first Bulgarian man to win an ATP Tour singles title. Since the 2024 US Open, Grigor Dimitrov became the male player with the longest active streak of consecutive Grand Slam appearances. Another thing about this Bulgarian athlete is that he’s the only male player from Bulgaria who reached US$1m. Dimitrov won the Bulgarian Sportsperson of the Year in 2014 and 2017. Both times he was the first (and still only) tennis player who won the award since its creation in 1958.
Dimitrov’s personal life is also spicy. He dated Maria Sharapova in late 2012, but they went public after the Madrid Open in 2013. That was his first win against world number one, Novak Đoković. The couple ended their romance in 2015. At the end of the same year, he started dating Nicole Scherzinger. Currently, he’s dating Lolita Osmanova.
4. Marat Safin
Safin is a retired Russian world number one tennis player. He reached the ATP number one singles ranking, as well as his sister Dinara Safina.
They are the only brother-sister tandem who achieved number-one rankings. Safin won his first Grand Slam title in 2000 at the US Open, defeating Pete Sampras. Marat also helped lead Russia to Davis Cup victories in 2002 and 2006. Another impressive thing about Safin is that he became the first Russian man to participate in the semi-finals of the Wimbledon Championship in 2008. Safin lost the game to Roger Federer. Also, in 2016, he became the first Russian tennis player to be introduced to the International Tennis Hall of Fame.
Marat Safin is currently single, and he likes it that way. Previously he dated Anna Druzyaka, Daria Zhukova, and Anastasiya Osipova. He retired from professional tennis in 2009 and is enjoying being single.
This ends our list of yummy tennis players in the 21st century. Maybe you’ll start watching tennis now if you aren’t already. We won’t judge your reasons.