

What Time Will Grigor Dimitrov Play Against Karen Khachanov?
Dimitrov and Khachanov are on the Day 5 Schedule at Miami Open Presented By Itau 2025 on Sunday 23 March 2025. Lets breakdown the career, past stats and recent form of these players and predict who will get the victory.
Who Will Win In This Head-To-Head?
Grigor Dimitrov, from Bulgaria, has a head-to-head record of 4-1 against Karen Khachanov. They have faced each other in various tournaments, including the Vienna (Austria) Hard R32, ATP Masters 1000 Paris (France) Hard R32, ATP Masters 1000 Shanghai (China) Hard R32, and the Marseille (France) Hard SF. In all of these matches, Dimitrov emerged as the winner. However, in their most recent encounter at the ATP Masters 1000 Paris (France) Hard QF, Khachanov defeated Dimitrov with a score of 6-2 6-3.
Dimitrov, aged 33, is currently ranked World No. 15 and has a career-high ranking of No. 3. In 2017, he ended the year at his career-high No. 3 after becoming the first debutant to go 5-0 en route to the Nitto ATP Finals title since McEnroe in 1978. He is the top-ranked Bulgarian player in history and the only champion from his country. Throughout his career, Dimitrov has won nine titles, including the 2017 ATP Masters 1000 Cincinnati. He reached a significant milestone in September 2023, surpassing 400 wins, which included his biggest victory over No. 1 Djokovic at the 2013 ATP Masters 1000 Madrid.
Dimitrov has had notable success in Grand Slam tournaments, reaching the semifinals at 2014 Wimbledon, 2017 Australian Open, and 2019 US Open. He has also reached 11 ATP Masters 1000 semifinals, including finals at the 2017 Cincinnati, 2023 Paris, and 2024 Miami. One significant highlight of his career was securing his first win in eight meetings with Federer in the 2019 US Open quarterfinals when he was ranked World No. 78. This victory made him the second-lowest-ranked US Open menโs semifinalist in history, with the record held by Connors at No. 174 in 1991.
In the current Miami tournament, Dimitrov aims to become the fourth active player to record 100 hard court ATP Masters 1000 wins, as he currently holds a record of 99-67. He is also looking to reach the fourth round in Miami for the 14th time, having reached that stage in 2012, 2016, and reaching the final in 2024. However, he is currently ranked No. 21 on the PIF ATP Rankings and would fall out of the top 20 for the first time since July 2023 if he were to lose in the third round.
Stefanos Tsitsipas
Arthur Fils
Alexander Zverev
Tallon Griekspoor
Carlos Alcaraz
Alex De Minaur
Karen Khachanov
Holger Rune
Cori Gauff
Jasmine Paolini
Jessika Ponchet
Elena Gabriela Ruse
Jelena Ostapenko
Iga Swiatek
Tiantsoa Rakotomanga Rajaonah
Suzan Lamens
Ekaterina Alexandrova
Jessica Pegula
Aryna Sabalenka
Elise Mertens
Fabian Marozsan
Zizou Bergs
Elina Svitolina
Jessica Bouzas Maneiro
Francisco Cerundolo
Ben Shelton
On the other hand, Karen Khachanov, aged 28, is ranked World No. 23 with a career-high ranking of No. 8, achieved in July 2019. In 2018, Khachanov achieved a significant breakthrough by upsetting top-10 players Isner, A. Zverev, Thiem, and Djokovic en route to winning the ATP Masters 1000 Paris title. He became the first unseeded ATP Masters 1000 champion since Nalbandian in 2007 Paris. However, after this impressive victory, Khachanov went on a 23-match losing streak against top-10 players from August 2019 to March 2023. He ended this streak by defeating No. 3 Tsitsipas and reaching the semifinals at the 2023 Miami ATP Masters 1000.
Khachanov has also had success in Grand Slam tournaments, advancing to the quarterfinals in all four events. His notable accomplishments include reaching the semifinals at the 2022 US Open and the 2023 Australian Open. Additionally, he represented Team ROC at the 2020 Tokyo Olympics, where he entered as the No. 4 menโs player and won the silver medal.
In the current Miami tournament, Khachanov is seeking his first top-20 win on outdoor hard courts since defeating No. 3 Tsitsipas in the 4th round two years ago. Previously, he had not reached the 4th round in Miami in his first six appearances, but he aims to reach this stage for the third consecutive year after reaching the semifinals in 2023 and the 4th round in 2024.
My Conclusion / Prediction:
My pick is that Dimitrov will win.
Matchstat.com has an Artificial Intelligence (Ai) prediction model that is trained on all professional ATP and WTA past matches.
To find out who our model thinks will win for Grigor Dimitrov vs Karen Khachanov, have a look at the prediction here:
Matchstat.com Grigor Dimitrov vs Karen Khachanov prediction.