Serena Williams‘s return to Wimbledon is the news of the hour for the tennis world. As the GOAT prepares to make her Grand Slam comeback, she reunited with a familiar face at SW19. Williams met her old friend, Grigor Dimitrov, upon arriving at the site, and the two shared a heartwarming moment. However, almost 14 years ago, Williams and Dimitrov were speculated to be more than just friends.

Coming into the 2026 Wimbledon Championships, Williams and Dimitrov were spotted together. The official Wimbledon Instagram handle shared a clip of them sharing a heartwarming hug and talking. Back in 2012, there were strong rumors that the duo was romantically linked. They were spotted together at vacation spots like Paris, and Williams was seen in Dimitrov’s box at the Miami Open. While it drew significant media attention, neither of them confirmed they were dating. Then in 2013, the Bulgarian started dating Maria Sharapova.

The bond between Dimitrov and Williams as friends has remained strong over the years. Williams attended Dimitrov’s matches even after her now-temporary retirement from professional tennis. Back in 2024, when Dimitrov had a resurgent run to the Miami final, Williams was spotted in the stands, cheering him on. She was also there during the 2024 US Open. After Dimitrov beat Andrey Rublev in a marathon five-setter, he thanked Williams in his on-court interview for giving him a motivational pep-talk on the day before the match.

Regardless of the authenticity of the rumors back then, it is not surprising the duo kept their personal lives low-profile to avoid added media scrutiny. Like the Williams-Dimitrov rumors, there was also speculation about a possible relationship between Nick Kyrgios and Eugenie Bouchard back in 2015, as the duo’s great on-court chemistry during Wimbledon mixed doubles put the rumor mill into overdrive. Even the duo of Tomas Machach and Katerina Siniakova did not confirm whether they were back together after sharing a kiss on the Olympic podium in 2024.

While Dimitrov and Williams have maintained their strong bond over the years, their objectives at this year’s Wimbledon aren’t very different either. One will be looking for an improbable comeback, the other will be looking for redemption after a heartbreak last year.

Serena Williams and Grigor Dimitrov Will Have Different Objectives at Wimbledon

The 2026 Wimbledon Championships signify something very different for Serena Williams and Grigor Dimitrov. For the 23-time Major champion, this is her big-time comeback into the sport on the biggest stage possible. She has played a couple of doubles events in the lead-up, but seeing her play singles on Center Court will be a moment for fans and Serena herself. The draw favors her, with Maya Jibade as her first-round opponent. However, the Australian is not to be taken lightly, as she is a capable grass-court player who won the Eastbourne title last year.

On the other hand, Dimitrov will hope for some redemption, as the Bulgarian suffered one of the most heartbreaking setbacks at Wimbledon last year. Playing as a huge underdog against top-seeded Jannik Sinner in the fourth round, the former World No.3 was on the cusp of a huge upset as he won the first two sets. However, the fairytale ended prematurely when the Bulgarian suffered a pectoral tear in the third set, forcing him to retire from the match.

Dimitrov sat out the rest of 2025 after that. In 2026, he’s had a poor start with a 2-8 record in singles and a 1-1 record in doubles so far, making his season debut on the ATP Challenger Tour while undergoing intensive injury recovery.

As for their resumes at Wimbledon, while Williams has won the Venus Rosewater Dish seven times in her career, Dimitrov’s best on the grass-court Major came in 2014, when he reached the semifinals, losing to Novak Djokovic. The coming fortnight will show if the two former greats still have it, with both Williams and Dimitrov hoping for a few good wins, if not for a deep run.