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Maria Sharapova Boyfriends: Dating History & Relationship Timeline

Maria Sharapova has remained one of the most visible figures in tennis, and public curiosity about her personal life often extends to her relationships. Here is a detailed look...

Mara Ellison Aug 04, 2026
Maria Sharapova Boyfriends: Dating History & Relationship Timeline

Maria Sharapova has remained one of the most visible figures in tennis, and public curiosity about her personal life often extends to her relationships. Here is a detailed look at her romantic history, structured for clarity and context without sensationalism.

The following overview provides a timeline of her most notable relationships, key identifiers, and how these connections fit into her public narrative.

Partner Connection to Sharapova Period Together Relationship Status
Jenson Brooksby Tennis player, began dating while competing on tour 2020 – 2022 Split
Grigor Dimitrov Tennis player, high-profile relationship widely covered 2015 – 2019 Split
Milos Raonic Montenegrin tennis player, shared professional environment 2014 – 2015 Split
Alexander Gilkes Entrepreneur, Paddle8 co-founder, long-term relationship 2012 – 2020 Engaged, never married

Romantic History with Alexander Gilkes

Maria Sharapova’s longest documented relationship was with Alexander Gilkes, a co-founder of the online auction house Paddle8. They began dating in 2012 and stayed together for eight years. During this period, they maintained a low profile compared to her on-court rivalries, though they occasionally appeared together at social events. They became engaged in 2018, but never married or publicly detailed wedding plans.

High-Profile Relationship with Grigor Dimitrov

In 2015, Sharapova began dating fellow tennis star Grigor Dimitrov. The relationship drew significant media attention due to their shared profession and the timing within her career. They were often seen together at tournaments and maintained an amicable public image. The couple separated in 2019, with both citing busy schedules and the demands of professional tennis as contributing factors.

Earlier Relationships and Brief Connections

Before her long-term commitments, Sharapova was linked with other athletes and public figures. Her short-lived romance with tennis player Milos Raonic in 2014 generated headlines but lasted only a few months. Another notable connection was with Jenson Brooksby, a younger player on the tour, which began in 2020 and ended in 2022. These relationships were less documented, reflecting her preference for privacy during earlier career stages.

Personal Life After Tennis

Since retiring from professional tennis, Sharapova has focused on business ventures, authorship, and family life. Public information about new romantic relationships has been limited, suggesting a shift toward personal stability away from the spotlight. Her past relationships, including those with Gilkes and Dimitrov, remain part of her public narrative but are balanced by her broader professional achievements.

Key Takeaways

  • Her longest relationship was with entrepreneur Alexander Gilkes.
  • She had high-profile relationships with fellow tennis players Grigor Dimitrov and Milos Raonic.
  • Her relationship with Jenson Brooksby occurred later in her career.
  • Sharapova has kept her personal life largely private, especially post-retirement.

FAQ

Reader questions

Who was Maria Sharapova’s most long-term boyfriend?

Alexander Gilkes, an entrepreneur and co-founder of Paddle8, was with Sharapova from 2012 to 2020, making him her longest documented partner.

Did Maria Sharapova ever marry a boyfriend?

No, she became engaged to Alexander Gilkes in 2018 but never married him or any other partner.

Who did Maria Sharapova date after turning professional?

In the early part of her professional career, she had brief links with tennis players such as Milos Raonic and later Jenson Brooksby, though these relationships were not as prominent.

Why did her relationship with Grigor Dimitrov end?

Both athletes cited the intense travel schedules and pressures of professional tennis as reasons for splitting up in 2019.

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