On Sunday, Bulgaria's 10th-seed Grigor Dimitrov will face Russia's fifth-seed Daniil Medvedev in the fourth round of Wimbledon.
The winner will face either 14th-seed Ben Shelton of the United States or top seed Jannik Sinner of Italy in the quarterfinals.
The pair is set for their second meeting this year, with Medvedev winning 6-4, 6-4 in the Indian Wells last-16. However, this will be their second meeting on grass after Dimitrov claimed a 6-3, 3-6, 6-3 victory in the Queen's Club quarterfinals in 2017.
All in all, Daniil Medvedev leads their head-to-head 7-3, but as mentioned above - Dimitrov holds a victory on grass.
Grigor Dimitrov's Wimbledon Journey saw him enjoying two straight-forward wins. He also passed a significant challenge in his second-round match against Juncheng Shang, where he had to fight back from two sets down. The 33-year-old Bulgarian started his Wimbledon campaign with a 6-3, 6-4, 7-5 victory over Dusan Lajovic of Serbia and probably anticipated another relatively routine win over Chinese teenager Shang Juncheng in the next round.
Unlike the different levels of effort in his second-round comeback against Shang Juncheng of China, Dimitrov enjoyed a comfortable 6-3, 6-4, 6-3 victory over French veteran Gael Monfils in the third round.
Dimitrov, a former world number three, won the Boys' Wimbledon title and an ATP grass-court title at Queen's Club, demonstrating his prowess on grass courts. Despite this, he has not reached the Wimbledon quarterfinals since his first slam semifinal in 2014. He attempted to reach another quarterfinal in 2017 and last year (2023) but was stopped by Roger Federer and Holger Rune, respectively.
Dimitrov seems more confident and determined, buoyed by recent successes, including a 5-4 record against Top-10 players in 2024 and a quarterfinal appearance at Roland Garros.
Beyond his semifinal appearance at Wimbledon twelve months ago, Daniil Medvedev has mostly been struggling at the All England Club and is now bidding to reach the quarterfinals for only the second time.
The Russian has faced significant disruptions due to rain at Wimbledon, most notably during his 2021 round-of-16 match against Hubert Hurkacz. The rain delay halted his momentum, and upon resumption the following day, he lost in five sets, missing out on his first Wimbledon quarterfinal. Recently, Medvedev overcame a similar challenge, defeating Jan-Lennard Struff in four sets despite rain delays, extending the match over two days. This victory indeed provided a sense of redemption.
Daniil Medvedev comes off a hard-fought win over an in-form Jan-Lennard Struff of Germany in the third round. The Russian won the opening two sets 6-1, 6-3, but the experienced German won the third and dragged Medvedev into a fourth-set tiebreaker.
Medvedev's efforts to improve his performance on grass culminated in his first Wimbledon semifinal last year. His journey to the semifinals was relatively unchallenged, aided by a retirement from Jiri Lehecka in the round of 16 and a victory over an inexperienced Christopher Eubanks in the quarterfinals.
However, this year presents a tougher challenge as he seeks to defend his semifinal points and maintain his top-four ranking.
In recent months, Medvedev has struggled with fitness, which has affected his performance. His French Open campaign ended in the round of 16 due to foot blisters, causing him to lose despite holding a set lead against Alex de Minaur. This was part of a series of setbacks, including a defeat after leading 2-0 against Jannik Sinner in the Australian Open final.
After suffering another heartbreaking defeat in the Australian Open final in January, Medvedev has yet to win a title in 2024. He also lost the Indian Wells Open final to Alcaraz and was once again stopped in the Miami Open semifinals by Jannik Sinner.
The upcoming match is poised to be a gripping encounter, with both players eager to advance further in the tournament and solidify their positions at the top of the game. While Grigor Dimitrov is arguably more adept on grass, his challenge lies in overcoming mental barriers against top-tier opponents on Major stages, a hurdle that has often hindered his career progress.
