Grigor Dimitrov’s amazing dating history, from Hollywood superstars to world’s sexiest tennis player and Love Islander

Published on July 08, 2025 at 07:28 AM

GRIGOR DIMITROV was flying high at Wimbledon and on course to cause another huge upset as he led Jannik Sinner by two sets.

However, with victory in sight,

Grigor Dimitrov playing a forehand at Wimbledon.
Grigor Dimitrov has a long dating history
Eiza González watching Grigor Dimitrov play tennis at Wimbledon.
Eiza Gonzalez has watched boyfriend Dimitrov at Wimbledon
Nicole Scherzinger and Grigor Dimitrov at the British Fashion Awards 2016.
Dimitrov has dated a string of high profile celebs including Nicole Scherzinger
Madalina Ghenea and Grigor Dimitrov at a photo call.
He dated supermodel Madalina Ghenea as recently as 2023
Ekin-Su Cülcüloğlu at the BAFTA Television Awards.
IN 2024 he was rumoured to be dating former Love Islander Ekin Su
Maria Sharapova at Wimbledon.
He also dated fellow tennis ace Maria Sharapova for three years

He was eventually forced to retire from the match due to a torn right pectoral muscle,

No1 seed Sinner paid tribute to his rival after his win by technicality, saying he couldn’t accept this “as a win”;.

Dimitrov has now been forced to retire from his last five grand slams.

But while injuries have seen him crumble on court, off it he continues to be a total love ace.

The Bulgarian is well known to have .

And in recent months rumours on his dating life have resurfaced.

He is rumoured to be in a burgeoning romance withHollywood actress , who has starred in Baby Driver and critically acclaimed show, Andor.

Dimitrov received a celebratory kiss from Eiza on the cheek after he defeated Nicolas Jarry to reach the fourth round.

Last year, the tennis star was reported to be dating Love Islander Ekin-Su Cülcüloğlu.

The 30-year-old shot to fame on Love Island in 2022, and was said to have agreed a string of secret romantic meet-ups with Dimitrov.

They are said to have been introduced to one another by mutual friends over the summer and have spent time in places such as , and whereGrigor lives, Monte Carlo.

A source told the Daily Mail: “They were just casually walking together in Paris, taking pictures with fans, and they were so friendly.”;

Before that in 2023 Dimitrov dated at the start of 2023, with the Romanian seen supporting her beau at some of the biggest games of his career.

Despite her busy schedule as a supermodel and actress, having starred asin the series House of Gucci and alongside Ed Westwick in Deep Fear, she was often courtside.

Dimitrov had spent some time as a single bachelor before that.

In 2020 he reportedly became the love interest of Lolita Osmanova, daughter of Russian billionaire and oligarch Eldar Osmanova and CEO of Luxury International Magazine.

She was spotted supporting her man at the Vienna Open 2020.

It is not known why their reported relationship ended.

He had ended a four-year relationship with , having started dating her in 2015.

The pair had gone public with their relationship in 2016.

Nicole was no stranger to having a public relationship after ending a long-term relationship with Formula One star Lewis Hamilton.

But from the moment their relationship became known, they faced scrutiny and rumours around whether they were still together.

Busy schedules and countless rumours of break-ups plagued their relationship, which eventually ended in 2019.

Dimitrov had tried dating another tennis pro in .

The pair dated for three years between 2012 and 2015 and seemed like the perfect match after going public in 2013.

The, at the time, was five years older than Grigor, who was only 23 during their relationship.

However, after three years together, the couple broke up due to their “split paths”;.

Dimitrov had also been rumoured to have dated women’s tennis GOAT, .

However, they never officially confirmed their relationship.

Grigor Dimitrov’s amazing dating history, from Hollywood superstars to world’s sexiest tennis player and Love Islander 2

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