Grigor Dimitrov and Lolita Osmanova may not be together, but the latter enjoys some good tennis and great vacations. As Daniil Medvedev stepped on the court of the Hard Rock Stadium to face Jannik Sinner, fans were surprised to see Osmanova accompany Medvedev’s wife. Extending her vacation in the US, the businesswoman recently shared a story on Instagram in which she can be seen chilling under the hot Miami sun and sipping beverages.

The fact that she was accompanied by Daniil Medvedev’s wife Daria adds another layer of speculation about her continued connection to the world of tennis. Her presence was even more surprising, considering Dimitrov was to play at the Miami Open.

Just a few days ago, when big names from the tennis world gathered around for the Indian Wells tournament in Southern California, Osmanova was seen enjoying her getaway to Joshua Tree National Park, which happened to be in an accessible location near the arena. Along with glamorously posing with the natural background, she also wrote a caption that said, “Lost in the desert”.

Although there was no official confirmation from either Dimitrov or Osmanova about their breakup, fans figured it out. There’s still no sign of the couple getting along once again, but her presence in the US has surely raised eyebrows. It is said that they were together for about three years.

Grigor Dimitrov’s short love story with Osmanova

Along with the achievements that he has added to his portfolio so far, Grigor Dimitrov’s dating history is also popular. Lolita, daughter of Russian billionaire Eldar Osmanova, spent a brief time with the Bulgarian ATP star.

Lolita found a lovable connection with Grigor in 2020 after she had to mark an end to her marriage with Gaspar Avdolyan. There were several moments when fans and media spotted both of them together. During the Vienna Open in 2020, she supported Dimitrov from the player’s box. But a few years later, their relationship started to dwindle.

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In 2023, rumors about the tennis star dating Romanian actress Madalina Ghenea were heard. They packed on the PDA during a romantic Italian getaway.

Dimitrov has had an active dating life. In fact, while there is no confirmation of this, he was rumored to be dating Serena Williams in 2012. He was also connected to Maria Sharapova and singer Nicole Scherzinger previously.

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