Novak Djokovic and Grigor Dimitrov set up oldest Masters 1000 SF in ATP history at Miami Open

Novak Djokovic and Grigor Dimitrov, who have etched their names into tennis history, have now added yet another milestone to their names as a due, highlighting the longevity of their careers. The Serb and the Bulgarian have set up a blockbuster clash in the semifinals of the 2025 Miami Open.

Djokovic and Dimitrov have been household names in the tennis fraternity for many years and have collected numerous accolades throughout their careers. Though the former may have the larger share of accolades, the latter has also enjoyed an illustrious career.

Djokovic ousted Rinky Hijikata, Camilo Ugo Carabelli, and 15th seed Lorenzo Musetti to reach the quarterfinals of the Miami Open, where he registered an impressive 6-3, 7-6(4) win over 24th seed Sebastian Korda 6-3, 7-6(4). On the other hand, the 33-year-old Dimitrov defeated Federico Cina, 22nd seed Karen Khachanov and 31st seed Brandon Nakashima before beating 23rd seed Francisco Cerundolo 6-7(6), 6-4, 7-6(3) in a topsy-turvy quarterfinal.

Djokovic and Dimitrov have a combined age of 71 years, making their Miami Open clash the oldest Masters 1000 semifinal in ATP history.

The two have faced one another 13 times before, with the Serb having a 12-1 head-to-head lead Despite this, he believes that his match against Dimitrov will be his toughest in Miami.

"I've got to be ready for the toughest match so far" - Novak Djokovic on his match against Grigor Dimitrov

Grigor Dimitrov and Novak Djokovic - Source: Getty

Novak Djokovic lauded the Bulgarian, citing how tough of an opponent he is, during his post-match on-court interview, stating that the match would be his toughest so far in Miami.

"I saw the match yesterday. Incredible fight, both players almost three hours in a grueling fight, saving match points. He deserves that, I mean, he works as hard as anybody, and I get along very well with Grigor, he's a good friend. Obviously, tomorrow on the court, we both want to win against each other, and we played so many times versus each other in all the tournaments, all the surfaces. He's such an experienced player and obviously in form, finals last year, semis now again this year. I've got to be ready for the toughest match so far."

The last match between the two came in the final of the 2023 Paris Masters, with Djokovic winning 6-4, 6-3. Whoever comes out on top, will take on either third seed Taylor Fritz or Jakub Mensik in the Miami Open final.