Who has Grigor Dimitrov dated?

• Grigor Dimitrov has a very interesting dating history, having previously dated a few tennis stars and a singer 
• His current girlfriend is Lolita Osmanova, the daughter of Russian billionaire Eldar Osmanova
• Lolita is the CEO of Luxury International Magazine and an ambassador of Monaco at the Berlin Iglesias Art

Grigor Dimitrov has a very interesting dating record and there have been a few speculations about who is his current girlfriend.

To begin with, Grigor Dimitrov is a Bulgarian professional tennis player who has been ranked as high as World No. 3 by the ATP. The 31-year-old is the highest-ranked Bulgarian tennis player in history. He is also the only Bulgarian male tennis player to reach the fourth round or better at a major in singles.

Grigor Dimitrov. Photo/ Eurosport.

As of now, Dimitrov has won eight ATP Tour singles titles. He became the first Bulgarian male tennis player to win an ATP Tour singles titles when he won the Stockholm Open in October 2013. The 31-year-old is an all-court player and is well-known for his athleticism and flexibility.

While starting his career, Dimitrov was compared to the legendary Roger Federer because of the similarity in their style of play and actions. As a result, he earned the nickname “Baby Fed”. Dimitrov met with Federer eight times and won only once when they met in 2019 at the US Open.

Well, Grigor Dimitrov’s personal life is always on the spotlight due to the number of women he has been romantically involved with.

Who Is Grigor Dimitrov’s Girlfriend? 

Lolita Osmanova is the current girlfriend of tennis star Grigor Dimitrov. Lolita, the daughter of Russian billionaire Eldar Osmanova, is the CEO of Luxury International Magazine. She is also an ambassador of Monaco at the Berlin Iglesias Art.

Lolita was born on January 26, 1996 in Moscow, Russia. She attended the International School of Moscow and later went to Rosinka Campus where she graduated. She stands 5 feet and 7 inches tall and her weight is around 56 kg.

Before getting into a relationship with Grigor Dimitrov, Lolita was briefly married to Gaspar Avdolyan, the son of telecom industry millionaire Albert Avdolyan. Lolita and Gaspar did their wedding at the iconic Dolby Theatre in Los Angeles in 2017. She was at the time 22 years old and their wedding was a grand function with a budget of around $10 million.

Lolita’s marriage to Gaspar Avdolyan would later fail and they separated barely a year after the wedding. Lolita has an Instagram account with over 100,000 followers.

When Did Grigor Dimitrov And Lolita Osmanova Begin Dating? 

The rumour of Grigor Dimitrov and Lolita Osmanova dating came out in 2020 during the Vienna Open. Lolita was spotted in the player’s box cheering for him.

The two made their relationship public via a social media post of a cosy picture including a board with ‘pont des amours’ or love bridge written on it. Grigor Dimitrov and his girlfriend Lolita have no children at the time of writing this article.

Grigor Dimitrov and Lolita Osmanova. Photo/ The SportsLite.

Who Has Grigor Dimitrov Dated?

Grigor Dimitrov has a very interesting dating history. Before getting into a relationship with his current girlfriend, Grigor Dimitrov dated former tennis player Maria Sharapova and American singer Nicole Scherzinger.

It is also rumoured that he dated retired tennis star Serena Williams. Grigor and Serena Williams dated for a short period of time in 2012, and they parted ways after Serena realized that Grigor was also dating Maria Sharapova.

The Bulgarian tennis star and Maria Sharapova went public about their relationship for the first time during the 2013 Madrid Open. Maria revealed that Dimitrov contacted her first through her agent.

Their relationship came to an end in July 2015. Maria felt she needed to focus more on her matches and move away from things that could have an impact on her career, thus ending the relationship.

At the end of 2015, Grigor Dimitrov began dating Nicole Scherzinger, American singer and leader of The Pussycat Dolls. The two made their relationship public for the first time in January 2016. They ended the relationship in 2019 after four years of dating.

Nicole confirmed that she was no longer the girlfriend of Grigor Dimitrov when she made a post on Instagram that read “I loved you at your darkest. Romans 5:8.”